Water → 1-(1-Hydroxy-1-methoxycarbonylmethyl)-3-(triphenyl methylamino)-4-(3-phenylprop-2-ynylthio)azetidin-2-one

HRID 1283695

Reaktionsgleichung

Reaktionsgleichung von HRID 1283695
[C:1]1([C:7]([NH:20][CH:21]2[CH:24]([S:25][CH2:26][C:27]#[C:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[NH:23][C:22]2=[O:35])([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:36]([O:40][CH3:41])(=[O:39])[CH:37]=[O:38].O>C1C=CC=CC=1>[OH:38][CH:37]([N:23]1[CH:24]([S:25][CH2:26][C:27]#[C:28][C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[CH:21]([NH:20][C:7]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:22]1=[O:35])[C:36]([O:40][CH3:41])=[O:39]

Komponenten

5

Edukt 3

HCID 962WaterHCID 70205Acetic acid, 2-oxo-, methyl esterHCID 215191773-(Triphenylmethylamino)-4-(3-phenylprop-2-ynylthio)azetidin-2-one

Produkt 1

HCID 537149641-(1-Hydroxy-1-methoxycarbonylmethyl)-3-(triphenyl methylamino)-4-(3-phenylprop-2-ynylthio)azetidin-2-oneAusbeute 64 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

3-(Triphenylmethylamino)-4-(3-phenylprop-2-ynylthio) azetidin-2-one (526mg) and methyl glyoxylate (1.17g) were refluxed in dry benzene (25ml) with provision for the removal of water. After 11/2 hours the solvent was evaporated and the residue was chromatographed on silica to give 1-(1-hydroxy-1-methoxycarbonylmethyl)-3-(triphenyl methylamino)-4-(3-phenylprop-2-ynylthio)azetidin-2-one as an amorphous solid (399 mg).

Aufarbeitung

  1. customAfter 11/2 hours the solvent was evaporated
  2. customthe residue was chromatographed on silica

Quellen und Nachweise

ORD-Eintrag
ord-2275ca3750914d6584a353e9dacf0d7a
Quelldatensatz
uspto-grants-1976_08
Patentnummer
US03975383

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