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

HRID 355446Notes

Reaction equation

HRID 355446 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

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10763140n-(Diphenylphosphinyl)-n-benzyl-d-alanine methyl esterHCID 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).

Workup

  1. customprepared
  2. customthe volatiles are removed
  3. customThe product is purified by silica gel flash chromatography (100% ethyl acetate)

Sources & evidence

ORD record
ord-724d59d30f78452d9deef8b465fb177e
Source dataset
uspto-grants-1998_11
Patent number
US05830915

Reaction notes

Loading…