1,4-Dioxane → (3S,4R)-4-(2-p-nitrobenzyloxycarbonylaminoethylthiothiocarbonylthio)-3-methoxy-2-oxoazetidine

HRID 1710251노트

반응식

HRID 1710251 반응식
[C:1](=[S:20])([S-:19])[S:2][CH2:3][CH2:4][NH:5][C:6]([O:8][CH2:9][C:10]1[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=1)=[O:7].[K+].C(O[C@@H:26]1[NH:29][C:28](=[O:30])[C@H:27]1[O:31][CH3:32])(=O)C.O1CCOCC1>O.P([O-])([O-])([O-])=O>[N+:16]([C:13]1[CH:14]=[CH:15][C:10]([CH2:9][O:8][C:6]([NH:5][CH2:4][CH2:3][S:2][C:1]([S:19][C@H:26]2[NH:29][C:28](=[O:30])[C@@H:27]2[O:31][CH3:32])=[S:20])=[O:7])=[CH:11][CH:12]=1)([O-:18])=[O:17]

참가 물질

6

반응물 3

HCID 312751,4-DioxaneHCID 23035703Potassium 2-p-nitrobenzyloxycarbonylaminoethyl trithiocarbonateHCID 56607243(3S,4S)-4-acetoxy-3-methoxy-2-oxoazetidine

생성물 1

HCID 56621546(3S,4R)-4-(2-p-nitrobenzyloxycarbonylaminoethylthiothiocarbonylthio)-3-methoxy-2-oxoazetidine

시약·촉매·용매 2

HCID 962Water용매HCID 1061Phosphate용매

실험 절차

A solution of 422 mg of potassium 2-p-nitrobenzyloxycarbonylaminoethyl trithiocarbonate in 1 ml of water is added dropwise at room temperature under, a nitrogen atmosphere to a solution of 159 mg (1 mmole) of (3S,4S)-4-acetoxy-3-methoxy-2-oxoazetidine in 3 ml of phosphate buffer of a pH of 7 and 0.2 ml of dioxan, and the mixture is stirred at the same temperature for 30 minutes. The reaction mixture is exhaustively extracted with methylene chloride. The combined organic phases are dried over sodium sulphate and concentrated by evaporation in vacuo. The residue is chromatographed over silica gel and yields the title compound with the following

후처리

  1. extractionThe reaction mixture is exhaustively extracted with methylene chloride
  2. dry with materialThe combined organic phases are dried over sodium sulphate
  3. concentrationconcentrated by evaporation in vacuo
  4. customThe residue is chromatographed over silica gel

출처 및 근거

ORD 기록
ord-3f1ec394cd984573a978c0518744473d
출처 데이터셋
uspto-grants-1990_08
특허 번호
US04952690

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