Hydrochloric Acid → N-hydroxy-2(R)-[[(R)-methylphenylphosphinyl]amino]-4-methylpentanamide

Reaction equation

C[O:2][C:3](=O)[C@@H:4]([CH2:15][CH:16]([CH3:18])[CH3:17])[NH:5][P@@:6]([CH3:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7].[NH2:20][O:21][K].Cl>>[OH:21][NH:20][C:3](=[O:2])[C@H:4]([NH:5][P@@:6]([CH3:14])([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:7])[CH2:15][CH:16]([CH3:18])[CH3:17]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 10636698n-((r)-Methylphenylphosphinyl)-d-leucine methyl ester

HCID 178514655HCID 178514655, compound

Product 1

HCID 10731747N-hydroxy-2(R)-[[(R)-methylphenylphosphinyl]amino]-4-methylpentanamide

Procedure

N-((R)-Methylphenylphosphinyl)-D-leucine methyl ester (60 mg, 0.21 mmol) is treated with a solution of NH2OK (0.57 mL, 1.76M in methanol) prepared as described in Fieser and Fieser, Vol. 1, p. 478. The reaction is stirred for 7 hours at which time TLC indicates completion. The reaction mixture is neutralized with 1M aqueous HCl and the volatiles are removed. The residue is purified by silica gel flash chromatography (95:5 ethyl acetate:ethanol) to give N-hydroxy-2(R)-[[(R)-methylphenylphosphinyl]amino]-4-methylpentanamide as a colorless solid: MS-IS m/z 285 [M+H]+.