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tetrabutylammonium (S)-3-(((benzyloxy)carbonyl)amino)-2-oxoazetidine-1-sulfonate → 2-Oxo-3-[N-chloro-N-[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid, tetrabutylammonium salt

HRID 371204
ノート
印刷プレビュー

反応式

HRID 371204 の反応式
[CH2:1]([N+:5]([CH2:14][CH2:15][CH2:16][CH3:17])([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:7][CH2:8][CH3:9])[CH2:2][CH2:3][CH3:4].[O:18]=[C:19]1[C@@H:22]([NH:23][C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:21][N:20]1[S:34]([O-:37])(=[O:36])=[O:35].O.O.O.O.O.O.O.O.O.O.B([O-])([O-])[O-].[Na+].[Na+].[Na+].[Cl:55][O-].[Na+]>C(Cl)Cl.O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>[CH2:14]([N+:5]([CH2:1][CH2:2][CH2:3][CH3:4])([CH2:6][CH2:7][CH2:8][CH3:9])[CH2:10][CH2:11][CH2:12][CH3:13])[CH2:15][CH2:16][CH3:17].[O:18]=[C:19]1[CH:22]([N:23]([Cl:55])[C:24]([O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[O:25])[CH2:21][N:20]1[S:34]([O-:37])(=[O:35])=[O:36]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 13575530tetrabutylammonium (S)-3-(((benzyloxy)carbonyl)amino)-2-oxoazetidine-1-sulfonateHCID 18377803Trisodium;borate;decahydrateHCID 23665760Sodium Hypochlorite

生成物 1

HCID 1317142682-Oxo-3-[N-chloro-N-[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid, tetrabutylammonium salt

試薬・触媒・溶媒 3

HCID 962Water
溶媒
HCID 6344Dichloromethane溶媒
HCID 62657Potassium Phosphate, Tribasic溶媒

実験手順

(S)-2-Oxo-3-[[(phenylmethoxy)carbonyl]amino]-1-azetidinesulfonic acid, tetrabutylammonium salt (0.9 g; see Example 4) dissolved in 80 ml of methylene chloride is added to a mixture (cooled to 0°-5° C.) of 3.17 g of sodium borate decahydrate and 11.8 ml of a 5.25% sodium hypochlorite solution in 70 ml of water. The reaction mixture is vigorously stirred for 55 minutes while cooling in an ice bath. After diluting the mixture with 0.5M monobasic potassium phosphate solution, the product is extracted with methylene chloride (three 150 ml portions). Combination of the extracts, drying (sodium sulfate), and removal of solvent in vacuo yields the title compound as an oil (0.94 g).

後処理

  1. temperaturewhile cooling in an ice bath
  2. extractionthe product is extracted with methylene chloride (three 150 ml portions)
  3. customCombination of the extracts, drying
  4. custom(sodium sulfate), and removal of solvent in vacuo

出典と根拠

ORDレコード
ord-0edc063335b74892acba27a8c0fa707e
出典データセット
uspto-grants-1985_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US04529698

反応ノート

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