methyl (2R)-2-(benzylamino)-3-hydroxypropanoate

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

Procedure: The title compound was prepared according to literature (ref. JOC, 1990, 55(1), 111-122) starting from (D)-serine methyl ester hydrochloride (98%, from Aldrich) (D)-serine methyl ester hydrochloride (10 g, 0.065 moles) was suspended in 50 ml of anhydrous methanol and cooled to 0° C. under nitrogen. Triethylamine (9 ml, 0.065 moles) was added dropwise, followed by benzaldehyde (6.6 ml, 0.065 moles). The reaction mixture was then warmed up and stirred at room temperature for 2 hours. Sodium borohydride (4.85 g, 0.13 moles) were added in small portions over 2 hours. The resulting mixture was stirred at room temperature overnight. The mixture was then slowly added to 50 ml of HCl (20% solution) at 0° C. and the resulting solution was washed with diethyl ether (50 ml). The aqueous layer was then brought to basic pH by adding solid potassium carbonate and extracted with diethyl ether (3×50 ml). The combined organic extracts were dried (Na2SO4) and concentrated under vacuum to afford the title compound as colourless oil (10.95 g). The title compound was prepared The reaction mixture was then warmed up The resulting mixture was stirred at room temperature overnight the resulting solution was washed with diethyl ether (50 ml) by adding solid potassium carbonate extracted with diethyl ether (3×50 ml) The combined organic extracts were dried (Na2SO4) concentrated under vacuum

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

Procedure: To methyl N-benzyl-D-serinate (1 eq.) in CH2Cl2 (0.3 M) at rt were added triethylamine (1 eq) and DMAP (0.05 eq). The reaction mixture was cooled to 0° C. and TBS-Cl (1.1 eq) was added. The reaction mixture was stirred at rt for 16 hrs, water was added and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with saturated aqueous NH4Cl, dried over Na2SO4, filtered and concentrated. The crude product was used as such for the next step. the aqueous layer was extracted with CH2Cl2 The combined organic layers were washed with saturated aqueous NH4Cl dried over Na2SO4 filtered concentrated

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

Procedure: To (2R)-3-hydroxy-1-methoxy-1-oxopropan-2-aminium chloride (1 eq.) in MeOH (1.3 M) at 0° C. was added triethylamine (1 eq.). The reaction mixture was stirred for 10 minutes and benzaldehyde (1 eq) was added. The reaction mixture was stirred for 2 hours and NaBH4 (1.5 eq.) was added portionwise to the reaction mixture over 30 min. The reaction mixture was stirred at rt for 5 hours and poured into a 1:1 mixture of saturated aqueous NH4Cl and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with brine and water, dried over Na2SO4, filtered and concentrated. The crude product was used as such for the next step. The reaction mixture was stirred for 2 hours The reaction mixture was stirred at rt for 5 hours The aqueous layer was extracted with EtOAc the combined organic layers were washed with brine and water dried over Na2SO4 filtered concentrated

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

Procedure: To (2R)-3-hydroxy-1-methoxy-1-oxopropan-2-aminium chloride (1 eq.) in MeOH (1.3 M) at 0° C. was added triethylamine (1 eq.). The reaction mixture was stirred for 10 minutes and benzaldehyde (1 eq) was added. The reaction mixture was stirred for 2 hours and NaBH4 (1.5 eq.) was added portionwise to the reaction mixture over 30 min. The reaction mixture was stirred at rt for 5 hours and poured into a 1:1 mixture of saturated aqueous NH4Cl and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with brine and water, dried over Na2SO4, filtered and concentrated. The crude product was used as such for the next step. The reaction mixture was stirred for 2 hours The reaction mixture was stirred at rt for 5 hours The aqueous layer was extracted with EtOAc the combined organic layers were washed with brine and water dried over Na2SO4 filtered concentrated

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

Procedure: The title compound was prepared according to literature (ref. JOC, 1990, 55(1), 111-122) starting from (D)-serine methyl ester hydrochloride (98%, from Aldrich) (D)-serine methyl ester hydrochloride (10 g, 0.065 moles) was suspended in 50 ml of anhydrous methanol and cooled to 0° C. under nitrogen. Triethylamine (9 ml, 0.065 moles) was added dropwise, followed by benzaldehyde (6.6 ml, 0.065 moles). The reaction mixture was then warmed up and stirred at room temperature for 2 hours. Sodium borohydride (4.85 g, 0.13 moles) were added in small portions over 2 hours. The resulting mixture was stirred at room temperature overnight. The mixture was then slowly added to 50 ml of HCl (20% solution) at 0° C. and the resulting solution was washed with diethyl ether (50 ml). The aqueous layer was then brought to basic pH by adding solid potassium carbonate and extracted with diethyl ether (3×50 ml). The combined organic extracts were dried (Na2SO4) and concentrated under vacuum to afford the title compound as colourless oil (10.95 g). The title compound was prepared The reaction mixture was then warmed up The resulting mixture was stirred at room temperature overnight the resulting solution was washed with diethyl ether (50 ml) by adding solid potassium carbonate extracted with diethyl ether (3×50 ml) The combined organic extracts were dried (Na2SO4) concentrated under vacuum

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

Procedure: The title compound was prepared according to literature (ref. JOC, 1990, 55(1), 111-122) starting from (D)-serine methyl ester hydrochloride (98%, from Aldrich) (D)-serine methyl ester hydrochloride (10 g, 0.065 moles) was suspended in 50 ml of anhydrous methanol and cooled to 0° C. under nitrogen. Triethylamine (9 ml, 0.065 moles) was added dropwise, followed by benzaldehyde (6.6 ml, 0.065 moles). The reaction mixture was then warmed up and stirred at room temperature for 2 hours. Sodium borohydride (4.85 g, 0.13 moles) were added in small portions over 2 hours. The resulting mixture was stirred at room temperature overnight. The mixture was then slowly added to 50 ml of HCl (20% solution) at 0° C. and the resulting solution was washed with diethyl ether (50 ml). The aqueous layer was then brought to basic pH by adding solid potassium carbonate and extracted with diethyl ether (3×50 ml). The combined organic extracts were dried (Na2SO4) and concentrated under vacuum to afford the title compound as colourless oil (10.95 g). The title compound was prepared The reaction mixture was then warmed up The resulting mixture was stirred at room temperature overnight the resulting solution was washed with diethyl ether (50 ml) by adding solid potassium carbonate extracted with diethyl ether (3×50 ml) The combined organic extracts were dried (Na2SO4) concentrated under vacuum

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

Procedure: The title compound was prepared according to literature (ref. JOC, 1990, 55(1), 111-122) starting from (D)-serine methyl ester hydrochloride (98%, from Aldrich) (D)-serine methyl ester hydrochloride (10 g, 0.065 moles) was suspended in 50 ml of anhydrous methanol and cooled to 0° C. under nitrogen. Triethylamine (9 ml, 0.065 moles) was added dropwise, followed by benzaldehyde (6.6 ml, 0.065 moles). The reaction mixture was then warmed up and stirred at room temperature for 2 hours. Sodium borohydride (4.85 g, 0.13 moles) were added in small portions over 2 hours. The resulting mixture was stirred at room temperature overnight. The mixture was then slowly added to 50 ml of HCl (20% solution) at 0° C. and the resulting solution was washed with diethyl ether (50 ml). The aqueous layer was then brought to basic pH by adding solid potassium carbonate and extracted with diethyl ether (3×50 ml). The combined organic extracts were dried (Na2SO4) and concentrated under vacuum to afford the title compound as colourless oil (10.95 g). The title compound was prepared The reaction mixture was then warmed up The resulting mixture was stirred at room temperature overnight the resulting solution was washed with diethyl ether (50 ml) by adding solid potassium carbonate extracted with diethyl ether (3×50 ml) The combined organic extracts were dried (Na2SO4) concentrated under vacuum

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

Procedure: The title compound was prepared according to literature (ref. JOC, 1990, 55(1), 111-122) starting from (D)-serine methyl ester hydrochloride (98%, from Aldrich) (D)-serine methyl ester hydrochloride (10 g, 0.065 moles) was suspended in 50 ml of anhydrous methanol and cooled to 0° C. under nitrogen. Triethylamine (9 ml, 0.065 moles) was added dropwise, followed by benzaldehyde (6.6 ml, 0.065 moles). The reaction mixture was then warmed up and stirred at room temperature for 2 hours. Sodium borohydride (4.85 g, 0.13 moles) were added in small portions over 2 hours. The resulting mixture was stirred at room temperature overnight. The mixture was then slowly added to 50 ml of HCl (20% solution) at 0° C. and the resulting solution was washed with diethyl ether (50 ml). The aqueous layer was then brought to basic pH by adding solid potassium carbonate and extracted with diethyl ether (3×50 ml). The combined organic extracts were dried (Na2SO4) and concentrated under vacuum to afford the title compound as colourless oil (10.95 g). m/z=210 [M+H]+ The title compound was prepared The reaction mixture was then warmed up The resulting mixture was stirred at room temperature overnight the resulting solution was washed with diethyl ether (50 ml) by adding solid potassium carbonate extracted with diethyl ether (3×50 ml) The combined organic extracts were dried (Na2SO4) concentrated under vacuum

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

Procedure: To methyl N-benzyl-D-serinate (1 eq.) in CH2Cl2 (0.3 M) at rt were added triethylamine (1 eq) and DMAP (0.05 eq). The reaction mixture was cooled to 0° C. and TBS-Cl (1.1 eq) was added. The reaction mixture was stirred at rt for 16 hrs, water was added and the aqueous layer was extracted with CH2Cl2. The combined organic layers were washed with saturated aqueous NH4Cl, dried over Na2SO4, filtered and concentrated. The crude product was used as such for the next step. the aqueous layer was extracted with CH2Cl2 The combined organic layers were washed with saturated aqueous NH4Cl dried over Na2SO4 filtered concentrated

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

Procedure: To (2R)-3-hydroxy-1-methoxy-1-oxopropan-2-aminium chloride (1 eq.) in MeOH (1.3 M) at 0° C. was added triethylamine (1 eq.). The reaction mixture was stirred for 10 minutes and benzaldehyde (1 eq) was added. The reaction mixture was stirred for 2 hours and NaBH4 (1.5 eq.) was added portionwise to the reaction mixture over 30 min. The reaction mixture was stirred at rt for 5 hours and poured into a 1:1 mixture of saturated aqueous NH4Cl and EtOAc. The aqueous layer was extracted with EtOAc and the combined organic layers were washed with brine and water, dried over Na2SO4, filtered and concentrated. The crude product was used as such for the next step. The reaction mixture was stirred for 2 hours The reaction mixture was stirred at rt for 5 hours The aqueous layer was extracted with EtOAc the combined organic layers were washed with brine and water dried over Na2SO4 filtered concentrated

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

Procedure: The title compound was prepared according to literature (ref. JOC, 1990, 55(1), 111-122) starting from (D)-serine methyl ester hydrochloride (98%, from Aldrich) (D)-serine methyl ester hydrochloride (10 g, 0.065 moles) was suspended in 50 ml of anhydrous methanol and cooled to 0° C. under nitrogen. Triethylamine (9 ml, 0.065 moles) was added dropwise, followed by benzaldehyde (6.6 ml, 0.065 moles). The reaction mixture was then warmed up and stirred at room temperature for 2 hours. Sodium borohydride (4.85 g, 0.13 moles) were added in small portions over 2 hours. The resulting mixture was stirred at room temperature overnight. The mixture was then slowly added to 50 ml of HCl (20% solution) at 0° C. and the resulting solution was washed with diethyl ether (50 ml). The aqueous layer was then brought to basic pH by adding solid potassium carbonate and extracted with diethyl ether (3×50 ml). The combined organic extracts were dried (Na2SO4) and concentrated under vacuum to afford the title compound as colourless oil (10.95 g). The title compound was prepared The reaction mixture was then warmed up The resulting mixture was stirred at room temperature overnight the resulting solution was washed with diethyl ether (50 ml) by adding solid potassium carbonate extracted with diethyl ether (3×50 ml) The combined organic extracts were dried (Na2SO4) concentrated under vacuum