3-Allyloxycarbonylamino-4-oxo-butyric acid tert-butyl ester → 3-Allyloxycarbonylamino-4-hydroxy-5-phenyl-pentanoic acid tert-butyl ester

Participants

Reaction Conditions

Reaction Steps

To a solution of benzylmagnesium chloride (20 mL, 20 mmol) in THF at −78° C. is added dropwise a 0° C. solution of 3-allyloxycarbonylamino-4-oxo-butyric acid tert-butyl ester, 102, (5.14 g, 20 mmol) in THF (100 mL). Once the addition is complete, the solution is allowed to warm to 0° C. over 30 minutes then the reaction mixture is poured into a beaker of crushed ice. The solution is extracted ×3 with CH2Cl2 (100 mL), the organic layers combined, dried over Na2SO4 and concentrated in vacuo to afford the desired product which is used without further purification.

Provenance & Evidence