chloromethyl (2S)-2-[(2-methylpropan-2-yl)oxycarbonylamino]propanoate

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

Procedure: To a vigorously stirred mixture of (S)-2-((tert-butoxycarbonyl)amino) propanoic acid (1 g, 5.29 mmol), tetrabutylammonium hydrogen sulfate (0.359 g, 1.057 mmol), and Na2CO3 (2.80 g, 26.4 mmol) in DCM 20 (mL) and water (20 mL), cooled in an ice/water bath, was slowly added chloromethyl chlorosulfate (1.09 mL, 10.57 mmol) over a 4 min period. After stirring in an ice/water bath for 30 min, the cold bath was removed and the reaction mixture was allowed to stir at room temperature. After stirring 16 h at room temperature the reaction mixture was diluted with water and extracted with DCM. The aqueous layer was back extracted with DCM and the combined organic layers were dried over MgSO4, filtered and concentrated. The crude material (1.64 g) was used as is without further purification. cooled in an ice/water bath over a 4 min the cold bath was removed to stir at room temperature After stirring 16 h at room temperature the reaction mixture was diluted with water extracted with DCM The aqueous layer was back extracted with DCM the combined organic layers were dried over MgSO4 filtered concentrated as is without further purification

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

Procedure: To a vigorously stirred mixture of (S)-2-((tert-butoxycarbonyl)amino) propanoic acid (1 g, 5.29 mmol), tetrabutylammonium hydrogen sulfate (0.359 g, 1.057 mmol), and Na2CO3 (2.80 g, 26.4 mmol) in DCM 20 (mL) and water (20 mL), cooled in an ice/water bath, was slowly added chloromethyl chlorosulfate (1.09 mL, 10.57 mmol) over a 4 min period. After stirring in an ice/water bath for 30 min, the cold bath was removed and the reaction mixture was allowed to stir at room temperature. After stirring 16 h at room temperature the reaction mixture was diluted with water and extracted with DCM. The aqueous layer was back extracted with DCM and the combined organic layers were dried over MgSO4, filtered and concentrated. The crude material (1.64 g) was used as is without further purification. cooled in an ice/water bath over a 4 min the cold bath was removed to stir at room temperature After stirring 16 h at room temperature the reaction mixture was diluted with water extracted with DCM The aqueous layer was back extracted with DCM the combined organic layers were dried over MgSO4 filtered concentrated as is without further purification

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

Procedure: To a vigorously stirred mixture of (S)-2-((tert-butoxycarbonyl)amino)propanoic acid (1 g, 5.29 mmol), tetrabutylammonium hydrogen sulfate (0.359 g, 1.057 mmol), and Na2CO3 (2.80 g, 26.4 mmol) in DCM 20 (mL) and water (20 mL) cooled in an ice/water bath was slowly added chloromethyl chlorosulfate (1.09 mL, 10.57 mmol) over a 4 min period. After stirring in ice/water bath for 30 min the cold bath was removed and the reaction allowed to stir at room temperature. After stirring 16 h at room temperature the reaction was diluted with water and extracted with DCM. The aqueous layer was back extracted with DCM and the combined organic layers were dried over MgSO4, filtered and concentrated to afford Preparation 5A (1.64 g). cooled in an ice/water bath over a 4 min was removed After stirring 16 h at room temperature the reaction was diluted with water extracted with DCM The aqueous layer was back extracted with DCM the combined organic layers were dried over MgSO4 filtered concentrated to afford

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

Procedure: To a vigorously stirred mixture of (S)-2-((tert-butoxycarbonyl)amino) propanoic acid (1 g, 5.29 mmol), tetrabutylammonium hydrogen sulfate (0.359 g, 1.057 mmol), and Na2CO3 (2.80 g, 26.4 mmol) in DCM 20 (mL) and water (20 mL), cooled in an ice/water bath, was slowly added chloromethyl chlorosulfate (1.09 mL, 10.57 mmol) over a 4 min period. After stirring in an ice/water bath for 30 min, the cold bath was removed and the reaction mixture was allowed to stir at room temperature. After stirring 16 h at room temperature the reaction mixture was diluted with water and extracted with DCM. The aqueous layer was back extracted with DCM and the combined organic layers were dried over MgSO4, filtered and concentrated. The crude material (1.64 g) was used as is without further purification. cooled in an ice/water bath over a 4 min the cold bath was removed to stir at room temperature After stirring 16 h at room temperature the reaction mixture was diluted with water extracted with DCM The aqueous layer was back extracted with DCM the combined organic layers were dried over MgSO4 filtered concentrated as is without further purification

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

Procedure: To a vigorously stirred mixture of (S)-2-((tert-butoxycarbonyl)amino) propanoic acid (1 g, 5.29 mmol), tetrabutylammonium hydrogen sulfate (0.359 g, 1.057 mmol), and Na2CO3 (2.80 g, 26.4 mmol) in DCM 20 (mL) and water (20 mL), cooled in an ice/water bath, was slowly added chloromethyl chlorosulfate (1.09 mL, 10.57 mmol) over a 4 min period. After stirring in an ice/water bath for 30 min, the cold bath was removed and the reaction mixture was allowed to stir at room temperature. After stirring 16 h at room temperature the reaction mixture was diluted with water and extracted with DCM. The aqueous layer was back extracted with DCM and the combined organic layers were dried over MgSO4, filtered and concentrated. The crude material (1.64 g) was used as is without further purification. cooled in an ice/water bath over a 4 min the cold bath was removed to stir at room temperature After stirring 16 h at room temperature the reaction mixture was diluted with water extracted with DCM The aqueous layer was back extracted with DCM the combined organic layers were dried over MgSO4 filtered concentrated as is without further purification

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

Procedure: To a vigorously stirred mixture of (S)-2-((tert-butoxycarbonyl)amino)propanoic acid (1 g, 5.29 mmol), tetrabutylammonium hydrogen sulfate (0.359 g, 1.057 mmol), and Na2CO3 (2.80 g, 26.4 mmol) in DCM 20 (mL) and water (20 mL) cooled in an ice/water bath was slowly added chloromethyl chlorosulfate (1.09 mL, 10.57 mmol) over a 4 min period. After stirring in ice/water bath for 30 min the cold bath was removed and the reaction allowed to stir at room temperature. After stirring 16 h at room temperature the reaction was diluted with water and extracted with DCM. The aqueous layer was back extracted with DCM and the combined organic layers were dried over MgSO4, filtered and concentrated to afford Preparation 5A (1.64 g). cooled in an ice/water bath over a 4 min was removed After stirring 16 h at room temperature the reaction was diluted with water extracted with DCM The aqueous layer was back extracted with DCM the combined organic layers were dried over MgSO4 filtered concentrated to afford