Formic Acid → N-hydroxy-2-[[methyl phenylphosphinyl](2-phenylethyl)-amino]-acetamide

HRID 355435Notes

Reaction equation

HRID 355435 reaction equation
C[O:2][C:3](=O)[CH2:4][N:5]([P:14]([CH3:22])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[NH2:24][O:25][K].C(O)=O.C(OCC)(=O)C>C(O)C>[OH:25][NH:24][C:3](=[O:2])[CH2:4][N:5]([P:14]([CH3:22])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:15])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 284Formic AcidHCID 8857Ethyl AcetateHCID 10806391n-(Methylphenylphosphinyl)-n-(2-phenylethyl)glycine methyl esterHCID 178514655HCID 178514655, compound

Product 1

HCID 10830393N-hydroxy-2-[[methyl phenylphosphinyl](2-phenylethyl)-amino]-acetamide

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

N-(Methylphenylphosphinyl)-N-(2-phenylethyl)glycine methyl ester (300 mg, 0.905 mmol) is treated with 0.77 mL of NH2OK (1.76M in methanol, solution prepared as described in Fieser and Fieser, Vol. 1, p. 478). The mixture is stirred for 3 hours at room temperature, neutralized with formic acid and concentrated. The crude product is purified by silica gel flash chromatography (85:15 ethyl acetate:ethanol) giving the product with slight impurities. Preparative TLC (90:10 ethyl acetate:ethanol) gives N-hydroxy-2-[[methyl phenylphosphinyl](2-phenylethyl)-amino]-acetamide as a colorless solid: MS-IS m/z 333 [M+H]+, 350 [M+NH4 ]+, 355 [M+Na]+, 371 [M+K]+. (R1 =phenyl ethyl, R2 =H, R3 =methyl, R4 =phenyl).

Workup

  1. concentrationconcentrated
  2. customThe crude product is purified by silica gel flash chromatography (85:15 ethyl acetate:ethanol)
  3. customgiving the product with slight impurities

Sources & evidence

ORD record
ord-d231838717394c229e3e81149e730383
Source dataset
uspto-grants-1998_11
Patent number
US05830915

Reaction notes

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