Dicyclohexylcarbodiimide → Acetyl-3-phenylthiopropionate

Participants

Reaction Steps

A pure sample of tertbutyl 3(R)-benzoylamino-2(S)-hydroxy-3-phenylthiopropionate was obtained via the same reaction sequence, but using the boron reagent di{[(1S,2S,5R)-2-isopropyl-5-methylcyclohex-1-yl]-methyl}boron bromide, derived from (-)menthone. Compound tertbutyl 3(R)-benzoylamino-2(S)-hydroxy-3-phenylthiopropionate was treated with excess (S)-(-)-α-methoxy-α-(trifluoromethyl) phenylacetic acid in dichloromethane in the presence of 1,3-dicyclohexylcarbodiimide (DCC) and catalytic 4-dimethylaminopyridine (DMAP). The Mosher derivative tertbutyl 3(R)-benzoylamino-2(S)-O-[(S)-α-methoxy-α-trifluoromethyl)phenyl]acetyl-3-phenylthiopropionate was obtained:

Provenance & Evidence