Hydrochloric Acid → N-hydroxy-2(R)-[[diphenylphosphinyl]benzylamino]-propionamide

Reaction equation

C[O:2][C:3](=O)[C@@H:4]([CH3:27])[N:5]([P:13]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH2:29][O:30][K].Cl>>[OH:30][NH:29][C:3](=[O:2])[C@H:4]([N:5]([P:13]([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14])[CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)[CH3:27]

Participants

Reactant 3

HCID 313Hydrochloric Acid

HCID 10763140n-(Diphenylphosphinyl)-n-benzyl-d-alanine methyl ester

HCID 178514655HCID 178514655, compound

Product 1

HCID 10620633N-hydroxy-2(R)-[[diphenylphosphinyl]benzylamino]-propionamide

Procedure

To N-(diphenylphosphinyl)-N-benzyl-D-alanine methyl ester (100 mg, 0.25 mmol) is added a solution of NH2OK (0.88 mL, 1.76M in methanol) prepared as described in Fieser and Fieser, Vol. 1, p. 478. The reaction is stirred for 16 hours at which time TLC indicates completion. The reaction mixture is neutralized with 1M aqueous HCl and the volatiles are removed. The product is purified by silica gel flash chromatography (100% ethyl acetate) to give N-hydroxy-2(R)-[[diphenylphosphinyl]benzylamino]-propionamide as an oil: MS-IS m/z 395 [M+H]+, 417 [M+Na]+. (R1 =benzyl, R2 =methyl, R3 =phenyl, R4 =phenyl).