tert-butyl N-[(2S)-1-hydroxy-3-phenylmethoxypropan-2-yl]carbamate

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (S)-tert-butyl 1-(benzyloxy)-3-hydroxypropan-2-ylcarbamate (1.89 g, 6.4 mmol) in DCM (50 mL) was added MsCl (0.55 mL, 7.04 mmol) followed by DIEA (1.27 mL, 7.68 mmol). The mixture was stirred at RT for 30 min and diluted with DCM (300 mL). The organic mixture washed with NaHCO3, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was then dissolved in DMF (20.0 mL). To the resulting solution was added NaN3 (1.25 g, 19.2 mmol) and the mixture was heated at 80° C. for 6 h. LCMS indicated the completion of the reaction. The mixture was cooled to RT and added water (20 mL) and EtOAc (200 mL). The organic layer was separated, washed with NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on silica gel column using a mixture of EtOAc and hexanes to give (S)-tert-butyl 1-azido-3-(benzyloxy)propan-2-ylcarbamate (1.5 g, 73% for 2 steps). The organic mixture washed with NaHCO3, brine dried over Na2SO4 filtered concentrated under reduced pressure The residue was then dissolved in DMF (20.0 mL) the mixture was heated at 80° C. for 6 h the completion of the reaction The mixture was cooled to RT The organic layer was separated washed with NaHCO3 and brine dried over Na2SO4 filtered concentrated under reduced pressure The residue was purified on silica gel column a mixture of EtOAc and hexanes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (S)-tert-butyl 1-(benzyloxy)-3-hydroxypropan-2-ylcarbamate (1.89 g, 6.4 mmol) in DCM (50 mL) was added MsCl (0.55 mL, 7.04 mmol) and DIEA (1.27 mL, 7.68 mmol). The mixture was stirred at RT for 30 min. The mixture was diluted with DCM (300 mL), washed with NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was dissolved in DMF (20 mL). To this DMF solution was added NaN3 (1.25 g, 19.2 mmol) and the mixture was heated to 80° C. for 6 h. LCMS indicated the completion of the reaction. The mixture was cooled to RT, water (20 mL) and EtOAc (200 mL) were added. The organic layer was separated, washed with NaHCO3, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The rude was purified on silica gel column to give (S)-tert-butyl 1-azido-3-(benzyloxy)propan-2-ylcarbamate (1.5 g, 73% for 2 steps). washed with NaHCO3 and brine dried over Na2SO4 filtered concentrated under reduced pressure The crude product was dissolved in DMF (20 mL) the mixture was heated to 80° C. for 6 h the completion of the reaction The mixture was cooled to RT The organic layer was separated washed with NaHCO3, brine dried over Na2SO4 filtered concentrated under reduced pressure The rude was purified on silica gel column

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (S)-tert-butyl 1-(benzyloxy)-3-hydroxypropan-2-ylcarbamate (1.89 g, 6.4 mmol) in DCM (50 mL) was added MsCl (0.55 mL, 7.04 mmol) followed by DIEA (1.27 mL, 7.68 mmol). The mixture was stirred at RT for 30 min and diluted with DCM (300 mL). The organic mixture washed with NaHCO3, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was then dissolved in DMF (20.0 mL). To the resulting solution was added NaN3 (1.25 g, 19.2 mmol) and the mixture was heated at 80° C. for 6 h. LCMS indicated the completion of the reaction. The mixture was cooled to RT and added water (20 mL) and EtOAc (200 mL). The organic layer was separated, washed with NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on silica gel column using a mixture of EtOAc and hexanes to give (S)-tert-butyl 1-azido-3-(benzyloxy)propan-2-ylcarbamate (1.5 g, 73% for 2 steps). The organic mixture washed with NaHCO3, brine dried over Na2SO4 filtered concentrated under reduced pressure The residue was then dissolved in DMF (20.0 mL) the mixture was heated at 80° C. for 6 h the completion of the reaction The mixture was cooled to RT The organic layer was separated washed with NaHCO3 and brine dried over Na2SO4 filtered concentrated under reduced pressure The residue was purified on silica gel column a mixture of EtOAc and hexanes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (S)-tert-butyl 1-(benzyloxy)-3-hydroxypropan-2-ylcarbamate (1.89 g, 6.4 mmol) in DCM (50 mL) was added MsCl (0.55 mL, 7.04 mmol) and DIEA (1.27 mL, 7.68 mmol). The mixture was stirred at RT for 30 min. The mixture was diluted with DCM (300 mL), washed with NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was dissolved in DMF (20 mL). To this DMF solution was added NaN3 (1.25 g, 19.2 mmol) and the mixture was heated to 80° C. for 6 h. LCMS indicated the completion of the reaction. The mixture was cooled to RT, water (20 mL) and EtOAc (200 mL) were added. The organic layer was separated, washed with NaHCO3, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The rude was purified on silica gel column to give (S)-tert-butyl 1-azido-3-(benzyloxy)propan-2-ylcarbamate (1.5 g, 73% for 2 steps). washed with NaHCO3 and brine dried over Na2SO4 filtered concentrated under reduced pressure The crude product was dissolved in DMF (20 mL) the mixture was heated to 80° C. for 6 h the completion of the reaction The mixture was cooled to RT The organic layer was separated washed with NaHCO3, brine dried over Na2SO4 filtered concentrated under reduced pressure The rude was purified on silica gel column

Conditions: temp:0.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: N-BOC-O-benzylserine (5.0 g, 16.9 mmol) in 30 mL dimethoxyethane was treated with 4-methylmorpholine (2.0 mL, 18.6 mmol) and cooled to 0° C. The solution was treated with isobutylchloroformate (2.3 mL, 17.8 mmol) and the resulting suspension stirred for 15 minutes, then filtered. The solids collected were washed with 2 portions of dimethoxyethane and the washings combined with the original filtrate. This material was cooled in an ice bath and treated with a cold solution of sodium borohydride (1.93 g, 50.8 mmol) in 40 mL 1/2 saturated sodium bicarbonate and the reaction stirred for 2 hours. The mixture was diluted with water and extracted with 3 portions of ethyl acetate. The combined organic extracts were washed with saturated aqueous sodium bicarbonate, water and brine, dried, filtered and concentrated to provide the title compound. MS (DCI, NH3): 282 (MH+); 299 (M+NH4)+. filtered The solids collected were washed with 2 portions of dimethoxyethane This material was cooled in an ice bath the reaction stirred for 2 hours extracted with 3 portions of ethyl acetate The combined organic extracts were washed with saturated aqueous sodium bicarbonate, water and brine dried filtered concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (S)-tert-butyl 1-(benzyloxy)-3-hydroxypropan-2-ylcarbamate (1.89 g, 6.4 mmol) in DCM (50 mL) was added MsCl (0.55 mL, 7.04 mmol) followed by DIEA (1.27 mL, 7.68 mmol). The mixture was stirred at RT for 30 min and diluted with DCM (300 mL). The organic mixture washed with NaHCO3, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was then dissolved in DMF (20.0 mL). To the resulting solution was added NaN3 (1.25 g, 19.2 mmol) and the mixture was heated at 80° C. for 6 h. LCMS indicated the completion of the reaction. The mixture was cooled to RT and added water (20 mL) and EtOAc (200 mL). The organic layer was separated, washed with NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on silica gel column using a mixture of EtOAc and hexanes to give (S)-tert-butyl 1-azido-3-(benzyloxy)propan-2-ylcarbamate (1.5 g, 73% for 2 steps). The organic mixture washed with NaHCO3, brine dried over Na2SO4 filtered concentrated under reduced pressure The residue was then dissolved in DMF (20.0 mL) the mixture was heated at 80° C. for 6 h the completion of the reaction The mixture was cooled to RT The organic layer was separated washed with NaHCO3 and brine dried over Na2SO4 filtered concentrated under reduced pressure The residue was purified on silica gel column a mixture of EtOAc and hexanes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (S)-tert-butyl 1-(benzyloxy)-3-hydroxypropan-2-ylcarbamate (1.89 g, 6.4 mmol) in DCM (50 mL) was added MSCl (0.55 mL, 7.04 mmol) and DIEA (1.27 mL, 7.68 mmol). The mixture was stirred at RT for 30 min. The mixture was diluted with DCM (300 mL), washed with NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was dissolved in DMF (20 mL). To this DMF solution was added NaN3 (1.25 g, 19.2 mmol) and the mixture was heated to 80° C. for 6 h. LCMS indicated the completion of the reaction. The mixture was cooled to RT, water (20 mL) and EtOAc (200 mL) were added. The organic layer was separated, washed with NaHCO3, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The rude was purified on silica gel column to give (S)-tert-butyl 1-azido-3-(benzyloxy)propan-2-ylcarbamate (1.5 g, 73% for 2 steps). washed with NaHCO3 and brine dried over Na2SO4 filtered concentrated under reduced pressure The crude product was dissolved in DMF (20 mL) the mixture was heated to 80° C. for 6 h the completion of the reaction The mixture was cooled to RT The organic layer was separated washed with NaHCO3, brine dried over Na2SO4 filtered concentrated under reduced pressure The rude was purified on silica gel column

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (S)-tert-butyl 1-(benzyloxy)-3-hydroxypropan-2-ylcarbamate (1.89 g, 6.4 mmol) in DCM (50 mL) was added MsCl (0.55 mL, 7.04 mmol) followed by DIEA (1.27 mL, 7.68 mmol). The mixture was stirred at RT for 30 min and diluted with DCM (300 mL). The organic mixture washed with NaHCO3, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was then dissolved in DMF (20.0 mL). To the resulting solution was added NaN3 (1.25 g, 19.2 mmol) and the mixture was heated at 80° C. for 6 h. LCMS indicated the completion of the reaction. The mixture was cooled to RT and added water (20 mL) and EtOAc (200 mL). The organic layer was separated, washed with NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on silica gel column using a mixture of EtOAc and hexanes to give (S)-tert-butyl 1-azido-3-(benzyloxy)propan-2-ylcarbamate (1.5 g, 73% for 2 steps). The organic mixture washed with NaHCO3, brine dried over Na2SO4 filtered concentrated under reduced pressure The residue was then dissolved in DMF (20.0 mL) the mixture was heated at 80° C. for 6 h the completion of the reaction The mixture was cooled to RT The organic layer was separated washed with NaHCO3 and brine dried over Na2SO4 filtered concentrated under reduced pressure The residue was purified on silica gel column a mixture of EtOAc and hexanes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (S)-tert-butyl 1-(benzyloxy)-3-hydroxypropan-2-ylcarbamate (1.89 g, 6.4 mmol) in DCM (50 mL) was added MsCl (0.55 mL, 7.04 mmol) and DIEA (1.27 mL, 7.68 mmol). The mixture was stirred at RT for 30 min. The mixture was diluted with DCM (300 mL), washed with NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was dissolved in DMF (20 mL). To this DMF solution was added NaN3 (1.25 g, 19.2 mmol) and the mixture was heated to 80° C. for 6 h. LCMS indicated the completion of the reaction. The mixture was cooled to RT, water (20 mL) and EtOAc (200 mL) were added. The organic layer was separated, washed with NaHCO3, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The rude was purified on silica gel column to give (S)-tert-butyl 1-azido-3-(benzyloxy)propan-2-ylcarbamate (1.5 g, 73% for 2 steps). washed with NaHCO3 and brine dried over Na2SO4 filtered concentrated under reduced pressure The crude product was dissolved in DMF (20 mL) the mixture was heated to 80° C. for 6 h the completion of the reaction The mixture was cooled to RT The organic layer was separated washed with NaHCO3, brine dried over Na2SO4 filtered concentrated under reduced pressure The rude was purified on silica gel column

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (S)-tert-butyl 1-(benzyloxy)-3-hydroxypropan-2-ylcarbamate (1.89 g, 6.4 mmol) in DCM (50 mL) was added MsCl (0.55 mL, 7.04 mmol) and DIEA (1.27 mL, 7.68 mmol). The mixture was stirred at RT for 30 min. The mixture was diluted with DCM (300 mL), washed with NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was dissolved in DMF (20 mL). To this DMF solution was added NaN3 (1.25 g, 19.2 mmol) and the mixture was heated to 80° C. for 6 h. LCMS indicated the completion of the reaction. The mixture was cooled to RT, water (20 mL) and EtOAc (200 mL) were added. The organic layer was separated, washed with NaHCO3, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The rude was purified on silica gel column to give (S)-tert-butyl 1-azido-3-(benzyloxy)propan-2-ylcarbamate (1.5 g, 73% for 2 steps). washed with NaHCO3 and brine dried over Na2SO4 filtered concentrated under reduced pressure The crude product was dissolved in DMF (20 mL) the mixture was heated to 80° C. for 6 h the completion of the reaction The mixture was cooled to RT The organic layer was separated washed with NaHCO3, brine dried over Na2SO4 filtered concentrated under reduced pressure The rude was purified on silica gel column

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (S)-tert-butyl 1-(benzyloxy)-3-hydroxypropan-2-ylcarbamate (1.89 g, 6.4 mmol) in DCM (50 mL) was added MsCl (0.55 mL, 7.04 mmol) followed by DIEA (1.27 mL, 7.68 mmol). The mixture was stirred at RT for 30 min and diluted with DCM (300 mL). The organic mixture washed with NaHCO3, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was then dissolved in DMF (20.0 mL). To the resulting solution was added NaN3 (1.25 g, 19.2 mmol) and the mixture was heated at 80° C. for 6 h. LCMS indicated the completion of the reaction. The mixture was cooled to RT and added water (20 mL) and EtOAc (200 mL). The organic layer was separated, washed with NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified on silica gel column using a mixture of EtOAc and hexanes to give (S)-tert-butyl 1-azido-3-(benzyloxy)propan-2-ylcarbamate (1.5 g, 73% for 2 steps). The organic mixture washed with NaHCO3, brine dried over Na2SO4 filtered concentrated under reduced pressure The residue was then dissolved in DMF (20.0 mL) the mixture was heated at 80° C. for 6 h the completion of the reaction The mixture was cooled to RT The organic layer was separated washed with NaHCO3 and brine dried over Na2SO4 filtered concentrated under reduced pressure The residue was purified on silica gel column a mixture of EtOAc and hexanes

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: To a solution of (S)-tert-butyl 1-(benzyloxy)-3-hydroxypropan-2-ylcarbamate (1.89 g, 6.4 mmol) in DCM (50 mL) was added MsCl (0.55 mL, 7.04 mmol) and DIEA (1.27 mL, 7.68 mmol). The mixture was stirred at RT for 30 min. The mixture was diluted with DCM (300 mL), washed with NaHCO3 and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The crude product was dissolved in DMF (20 mL). To this DMF solution was added NaN3 (1.25 g, 19.2 mmol) and the mixture was heated to 80° C. for 6 h. LCMS indicated the completion of the reaction. The mixture was cooled to RT, water (20 mL) and EtOAc (200 mL) were added. The organic layer was separated, washed with NaHCO3, brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The rude was purified on silica gel column to give (S)-tert-butyl 1-azido-3-(benzyloxy)propan-2-ylcarbamate (1.5 g, 73% for 2 steps). washed with NaHCO3 and brine dried over Na2SO4 filtered concentrated under reduced pressure The crude product was dissolved in DMF (20 mL) the mixture was heated to 80° C. for 6 h the completion of the reaction The mixture was cooled to RT The organic layer was separated washed with NaHCO3, brine dried over Na2SO4 filtered concentrated under reduced pressure The rude was purified on silica gel column