Hydrochloric Acid → HCID 88133247, compound

HRID 355454Notes

Reaction equation

HRID 355454 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 10545464HCID 10545464, compoundHCID 178514655HCID 178514655, compound

Product 1

HCID 88133247HCID 88133247, compoundYield 33%

Procedure

N-((R)-Ethylphenylphosphinyl)-N-benzyl-D-alanine methyl ester (333 mg, 0.96 mmol) is treated with a solution of NH2OK (3.3 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 110 mg (33%) of N-hydroxy-2(R)-[[(R)-ethylphenyl-phosphinyl]amino]-propionamide as colorless solid: MS-IS m/z 347 [M+H]+, 369 [M+Na]+. (R1 =benzyl, R2 =methyl, R3 =ethyl, R4 =phenyl).

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-22b3b79caafc47ee9be65bdde4c07ae7
Source dataset
uspto-grants-1998_11
Patent number
US05830915

Reaction notes

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