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

HRID 1578893

반응식

HRID 1578893 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 241Benzene용매

실험 절차

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). νmax (CHCl3) 3475 (--OH), 1770 (β-lactam), 1750 (ester) cm-1.

후처리

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

출처 및 근거

ORD 기록
ord-3cc90c8cd3aa4749b64a735c745c1059
출처 데이터셋
uspto-grants-1976_02
특허 번호
US03939157

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