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

HRID 355435ノート

反応式

HRID 355435 の反応式
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

参加物

6

反応物 4

HCID 284Formic AcidHCID 8857Ethyl AcetateHCID 10806391n-(Methylphenylphosphinyl)-n-(2-phenylethyl)glycine methyl esterHCID 178514655HCID 178514655、化合物

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-d231838717394c229e3e81149e730383
出典データセット
uspto-grants-1998_11
特許番号
US05830915

反応ノート

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