tert-butyl N-[(2R)-1-hydroxy-3-phenylpropan-2-yl]carbamate

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

Procedure: A cold solution (0° C.) of N-Boc-D-phenylalaninol (0.53 g, 2.09 mmol) in anhydrous methylene chloride (20 mL) was treated sequentially with methanesulfonyl chloride (360 mg, 3.14 mmol) and triethylamine (0.32 g, 3.14 mmol). The reaction was stirred at 0° C. for 2 hr, quenched with 1M hydrochloric acid (2×25 mL) and extracted with methylene chloride. The combined extract was washed with saturated sodium bicarbonate (1×25 mL), and brine (1×25 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and the filtrate adsorbed onto silica gel and applied to a column prepacked with silica gel. The title compound was eluted from the column with hexane:ethyl acetate (60:40, v:v) to furnish titled compound (352 mg) as a white solid. quenched with 1M hydrochloric acid (2×25 mL) extracted with methylene chloride The combined extract was washed with saturated sodium bicarbonate (1×25 mL), and brine (1×25 mL) The organic layer was dried over anhydrous sodium sulfate filtered The title compound was eluted from the column with hexane:ethyl acetate (60:40, v:v)

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

Procedure: A cooled solution of (R)-2-(tert-butoxycarbonylamino)-3-phenyl-1-propanol (92) (1 g, 4 mmol) in CH2Cl2 (20 ml) at 0° C. was treated with triethylamine (1.12 m, 8 mmol), pivaloyl chloride (0.74 ml, 6 mmol) followed by 4-(dimethylamino)pyridine (50 mg 0.4 mmol) and stirred overnight at room temperature. The mixture was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel with EtOAc/hexanes (1:4) as an eluant to give compound 94. The mixture was concentrated in vacuo the residue was purified by flash column chromatography on silica gel with EtOAc/hexanes (1:4) as an eluant

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

Procedure: A cooled solution of (R)-2-(tert-butoxycarbonylamino)-3-phenyl-1-propanol (92) (1 g, 4 mmol) in CH2Cl2 (20 ml) at 0° C. was treated with triethylamine (1.12 m, 8 mmol), pivaloyl chloride (0.74 ml, 6 mmol) followed by 4-(dimethylamino)pyridine (50 mg 0.4 mmol) and stirred overnight at room temperature. The mixture was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel with EtOAc/hexanes (1:4) as an eluant to give compound 94. The mixture was concentrated in vacuo the residue was purified by flash column chromatography on silica gel with EtOAc/hexanes (1:4) as an eluant

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

Procedure: To a solution of N-tert-butoxycarbonyl-D-Phenylalaninol (754 mg) and TEA (0.5 ml) in dichloromethane was added methanesulfonyl chloride (0.28 ml) at 0°~5° C. The reaction mixture was stirred at 0°~5° C. for 30 min, quenched with water, and extracted with dichloromethane. The organic layer was washed with 10% citric acid and sat. NaHCO3, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate/hexane=1/2 to afford the product (931 mg). quenched with water extracted with dichloromethane The organic layer was washed with 10% citric acid and sat. NaHCO3 dried over MgSO4 filtered concentrated under reduced pressure The residue was crystallized from ethyl acetate/hexane=1/2

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

Procedure: To a solution of N-tert-butoxycarbonyl-D-Phenylalaninol (754 mg) and TEA (0.5 ml) in dichloromethane was added methanesulfonyl chloride (0.28 ml) at 0°~5° C. The reaction mixture was stirred at 0°~5° C. for 30 min, quenched with water, and extracted with dichloromethane. The organic layer was washed with 10% citric acid and sat. NaHCO3, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate/hexane=1/2 to afford the product (931 mg). quenched with water extracted with dichloromethane The organic layer was washed with 10% citric acid and sat. NaHCO3 dried over MgSO4 filtered concentrated under reduced pressure The residue was crystallized from ethyl acetate/hexane=1/2

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

Procedure: To a solution of N-tert-butoxycarbonyl-D-Phenylalaninol (754 mg) and TEA (0.5 ml) in dichloromethane was added methanesulfonyl chloride (0.28 ml) at 0°-5° C. The reaction mixture was stirred at 0°-5° C. for 30 min, quenched with water, and extracted with dichloromethane. quenched with water extracted with dichloromethane

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

Procedure: To a solution of N-tert-butoxycarbonyl-D-Phenylalaninol (754 mg) and TEA (0.5 ml) in dichloromethane was added methanesulfonyl chloride (0.28 ml) at 0°-5° C. The reaction mixture was stirred at 0°-5° C. for 30 min, quenched with water, and extracted with dichloromethane. quenched with water extracted with dichloromethane

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

Procedure: A cold solution (0° C.) of N-Boc-D-phenylalaninol (0.53 g, 2.09 mmol) in anhydrous methylene chloride (20 mL) was treated sequentially with methanesulfonyl chloride (360 mg, 3.14 mmol) and triethylamine (0.32 g, 3.14 mmol). The reaction was stirred at 0° C. for 2 hr, quenched with 1M hydrochloric acid (2×25 mL) and extracted with methylene chloride. The combined extract was washed with saturated sodium bicarbonate (1×25 mL), and brine (1×25 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and the filtrate adsorbed onto silica gel and applied to a column prepacked with silica gel. The title compound was eluted from the column with hexane:ethyl acetate (60:40, v:v) to furnish titled compound (352 mg) as a white solid. quenched with 1M hydrochloric acid (2×25 mL) extracted with methylene chloride The combined extract was washed with saturated sodium bicarbonate (1×25 mL), and brine (1×25 mL) The organic layer was dried over anhydrous sodium sulfate filtered The title compound was eluted from the column with hexane:ethyl acetate (60:40, v:v)

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

Procedure: To a solution of N-tert-butoxycarbonyl-D-Phenylalaninol (754 mg) and TEA (0.5 ml) in dichloromethane was added methanesulfonyl chloride (0.28 ml) at 0°~5 ° C. The reaction mixture was stirred at 0°~5 ° C. for 30 min, quenched with water, and extracted with dichloromethane. The organic layer was washed with 10% citric acid and sat. NaHCO, dried over MgSO4, filtered, and concentrated under reduced pressure. The residue was crystallized from ethyl acetate/hexane=1/2 to afford the product (931 mg). quenched with water extracted with dichloromethane The organic layer was washed with 10% citric acid and sat. NaHCO dried over MgSO4 filtered concentrated under reduced pressure The residue was crystallized from ethyl acetate/hexane=1/2

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

Procedure: In a 500 mL flask equipped with magnetic stirrer, N-(t-butyloxycarbonyl)-(D)-phenylalaninol(0.040 mole, 10.05 g) was dissolved in 200 mL of THf and was added with NaH(0.048 mole, 1.15 g) at 0° C. The reaction mixture was stirred at 0° C. for 1 hour, followed by the addition of CS2 (0.048 mole, 3.65 g). After being stirred for 40 min. at 0° C., MeI(0.048 mole, 6.81 g) was added to the reaction mixture. The reaction mixture was stirred at room temperature for 2 hours, followed by the addition of 5N NH4OH (0.090 mole, 18.0 mL) for 6 hours. The resulting solution was quenched with water. The organic layer was extracted 3 times with dichloromethane, dried over magnesium sulfate and distilled in vacuo, to give a solid. This was recrystalized in a solution mixture of n-hexane and diethyl ether, to produce 11.3 g of O-thiocarbamoyl-N-(t-butyloxycarbonyl)-(D)-phenylalaninol: Yield 78%. In a 500 mL flask equipped with magnetic stirrer After being stirred for 40 min. at 0° C. The reaction mixture was stirred at room temperature for 2 hours The resulting solution was quenched with water The organic layer was extracted 3 times with dichloromethane dried over magnesium sulfate distilled in vacuo to give a solid This was recrystalized in a solution mixture of n-hexane and diethyl ether

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

Procedure: A cold solution (0° C.) of N-Boc-D-phenylalaninol (0.53 g, 2.09 mmol) in anhydrous methylene chloride (20 mL) was treated sequentially with methanesulfonyl chloride (360 mg, 3.14 mmol) and triethylamine (0.32 g, 3.14 mmol). The reaction was stirred at 0° C. for 2 hr, quenched with 1M hydrochloric acid (2×25 mL) and extracted with methylene chloride. The combined extract was washed with saturated sodium bicarbonate (1×25 mL), and brine (1×25 mL). The organic layer was dried over anhydrous sodium sulfate, filtered and the filtrate adsorbed onto silica gel and applied to a column prepacked with silica gel. The title compound was eluted from the column with hexane:ethyl acetate (60:40, v:v) to furnish titled compound (352 mg) as a white solid. quenched with 1M hydrochloric acid (2×25 mL) extracted with methylene chloride The combined extract was washed with saturated sodium bicarbonate (1×25 mL), and brine (1×25 mL) The organic layer was dried over anhydrous sodium sulfate filtered The title compound was eluted from the column with hexane:ethyl acetate (60:40, v:v)

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

Procedure: A cooled solution of (R)-2-(tert-butoxycarbonylamino)-3-phenyl-1-propanol (92) (1 g, 4 mmol) in CH2Cl2 (20 ml) at 0° C. was treated with triethylamine (1.12 m, 8 mmol), pivaloyl chloride (0.74 ml, 6 mmol) followed by 4-(dimethylamino)pyridine (50 mg 0.4 mmol) and stirred overnight at room temperature. The mixture was concentrated in vacuo and the residue was purified by flash column chromatography on silica gel with EtOAc/hexanes (1:4) as an eluant to give compound 94. The mixture was concentrated in vacuo the residue was purified by flash column chromatography on silica gel with EtOAc/hexanes (1:4) as an eluant