Benzyl chloroformate → HCID 10978298, compound

Participants

Reaction Conditions

Reaction Steps

A mixture of 25.16 g (112 mmol) of (2S,3R)-2-trifluoroacetylamino-3-methyl-4-pentenoic acid and 112 mL of 2 N aqueous sodium hydroxide is stirred at 80° C. for 1.5 h. The mixture is then allowed to cool to 25° C. and is further chilled to 0° C. 2 N aqueous sodium hydroxide (112 mL) is added followed by dropwise addition of 18 mL (126 mmol) of benzyl chloroformate. After 45 min at 0° C. and 5 h at 25° C. the mixture is added to 150 mL of water and is treated with aqueous sodium hydroxide until an orange solution resulted. The mixture is extracted with ether. The aqueous phase is acidified with 6 N HCl to pH 1 and is extracted with ether. Drying over magnesium sulfate and concentration in vacuo affords 22.61 g (77%) of (2S,3R)-2-benzyloxycarbonylamino-3-methyl-4-pentenoic acid as an oil.

Provenance & Evidence