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

HRID 355435Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 355435
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

Komponenten

6

Edukt 4

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-d231838717394c229e3e81149e730383
Quelldatensatz
uspto-grants-1998_11
Patentnummer
US05830915

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