L-Lactic Acid → HCID 86759847, compound

Participants

Reaction Steps

1.42 (5 mmol) of (R)-1-benzyloxycarbonylamino-2-phenylethane boronic acid (V) is refluxed with 80 ml of benzene and 0.45 g (5 mmol) of (S)-(+)-lactic acid (VI) in a Dean Stark apparatus for 5 hrs. After cooling the mixture is concentrated, redissolved in 75 ml of methanol and then transferred to a two-necked flask. The mixture is flushed with nitrogen, 1 gram of 10% palladium on activated carbon is added and hydrogen gas is passed through the stirred mixture for 2 hrs. 75 ml of methanol-water (1:1 v /v) is added and the mixture filtered slowly through celite (30 g). The filtrate is collected and concentrated to give (S)-lactate-1-(R)-amino-2-phenylethane boronate (VIII).

Provenance & Evidence