Hydrochloric Acid → N-hydroxy-2(R)-[[(S)-ethylphenylphosphinyl]amino]-propionamide

HRID 355453Notes

Reaction equation

HRID 355453 reaction equation
C[O:2][C:3](=O)[C@@H:4]([CH3:23])[N:5]([P@:13]([CH2:21][CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14])CC1C=CC=CC=1.[NH2:25][O:26][K].Cl>>[OH:26][NH:25][C:3](=[O:2])[C@H:4]([NH:5][P@:13]([CH2:21][CH3:22])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:14])[CH3:23]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 10831357n-((s)-Ethylphenylphosphinyl)-n-benzyl-d-alanine methyl esterHCID 178514655HCID 178514655, compound

Product 1

HCID 88138459N-hydroxy-2(R)-[[(S)-ethylphenylphosphinyl]amino]-propionamide

Procedure

N-((S)-Ethylphenylphosphinyl)-N-benzyl-D-alanine methyl ester (105 mg, 0.30 mmol) is treated with a solution of NH2OK (1.0 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 residue is purified by silica gel flash chromatography (95:5 ethyl acetate:methanol) to give N-hydroxy-2(R)-[[(S)-ethylphenylphosphinyl]amino]-propionamide as colorless solid: MS-IS m/z 347 [M+H]+, 369 [M+Na]+.

Workup

  1. customprepared
  2. customthe volatiles are removed
  3. customThe residue is purified by silica gel flash chromatography (95:5 ethyl acetate:methanol)

Sources & evidence

ORD record
ord-b3b00270adc34f1a845980618a85e3f8
Source dataset
uspto-grants-1998_11
Patent number
US05830915

Reaction notes

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