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

반응식

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]

참가 물질

반응물 3

HCID 313Hydrochloric Acid

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

HCID 178514655HCID 178514655, 화합물

생성물 1

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

실험 절차

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]+.