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Water → diphenylmethyl (6R,7R)-3-[(methylsulfonyl)oxy]-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate

HRID 28404
ノート
印刷プレビュー

反応式

HRID 28404 の反応式
[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:35](=[O:36])[N:13]3[C:14]([C:19]([O:21][CH:22]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)=[O:20])=[C:15]([OH:18])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:37][S:38](Cl)(=[O:40])=[O:39].C(N(C(C)C)C(C)C)C.O>CC(C)=O>[C:1]1([CH2:7][C:8]([NH:10][C@@H:11]2[C:35](=[O:36])[N:13]3[C:14]([C:19]([O:21][CH:22]([C:23]4[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=4)[C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=4)=[O:20])=[C:15]([O:18][S:38]([CH3:37])(=[O:40])=[O:39])[CH2:16][S:17][C@H:12]23)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 31297Methanesulfonyl chlorideHCID 81531DiisopropylethylamineHCID 54721268(6R,7R)-benzhydryl 3-hydroxy-8-oxo-7-(2-phenylacetamido)-5-thia-1-azabicyclo(4.2.0)oct-2-ene-2-carboxylate

生成物 1

HCID 11050121diphenylmethyl (6R,7R)-3-[(methylsulfonyl)oxy]-8-oxo-7-[(phenylacetyl)amino]-5-thia-1-azabicyclo[4.2.0]oct-2-ene-2-carboxylate
収率 90%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

反応条件

温度
-20 °C

実験手順

Benzhydryl 7β-[(phenylacetyl)amino]-3-hydroxy-3-cephem-4-carboxylate (500 g, 1 mol) was dissolved in acetone (2 L) and methanesulfonyl chloride (86 mL, 1.1 mol) was added dropwise over 10 min with stirring at −20° C. Then, ethyldiisopropylamine (183 mL, 1.05 mol) was added dropwise over 30 min and the mixture was stirred at −20° C. for 40 min. The reaction mixture was poured into iced water (8 L) and the precipitate was collected by filtration. The precipitate was then washed with water (2 L) and ethyl acetate (300 mL), and dried under reduced pressure to give the title compound (523 g, 0.90 mol). yield: 90%.

後処理

  1. stirringthe mixture was stirred at −20° C. for 40 min
  2. filtrationthe precipitate was collected by filtration
  3. washThe precipitate was then washed with water (2 L) and ethyl acetate (300 mL)
  4. customdried under reduced pressure

出典と根拠

ORDレコード
ord-83ad514004584cea9af9411667cdca7c
出典データセット
uspto-grants-2008_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07419973B2

反応ノート

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