Lithium Hydroxide → (cis)-1-Benzoyl-4-fluoro-L-proline

Participants

Reaction Steps

To a solution of Part A (cis)-1-benzoyl-4-fluoro-L-proline methyl ester (3.7 g, 14.74 mmole) in tetrahydrofuran-water (37 ml-7 ml) was added 31 ml of a 1N solution of lithium hydroxide in water. The reaction was stirred at room temperature for 2 hours. The tetrahydrofuran was evaporated, the pH of the residual aqueous solution was adjusted to 8 and extracted with ethyl acetate. The organic extracts were discarded. The aqueous phase was acidified to pH 2 with concentrated HCl and extracted with dichloromethane. The organic extracts were washed with brine and dried (sodium sulfate). The organic solution was filtered and concentrated to 2.9 g of solid.

Provenance & Evidence