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

HRID 1710251ノート

反応式

HRID 1710251 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 1061Phosphate溶媒

実験手順

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

後処理

  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

出典と根拠

ORDレコード
ord-3f1ec394cd984573a978c0518744473d
出典データセット
uspto-grants-1990_08
特許番号
US04952690

反応ノート

読み込み中…