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m-Chloroperbenzoic acid → (1R,2S,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzylsulfinyl)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

HRID 130503
ノート
印刷プレビュー

反応式

HRID 130503 の反応式
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH2:12]([O:14][C:15]([C@:17]1([N:39]=[N+:40]=[N-:41])[C@H:22]([S:23][CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)[CH2:21][C@@H:20]2[C@H:18]1[C@@:19]2([F:38])[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:16])[CH3:13]>ClCCl>[CH2:12]([O:14][C:15]([C@:17]1([N:39]=[N+:40]=[N-:41])[C@H:22]([S:23]([CH2:24][C:25]2[CH:30]=[CH:29][C:28]([Cl:31])=[C:27]([Cl:32])[CH:26]=2)=[O:9])[CH2:21][C@@H:20]2[C@H:18]1[C@@:19]2([F:38])[C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:16])[CH3:13]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 70297m-Chloroperbenzoic acid2 回HCID 86606014(1R,2S,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzylsulfanyl)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester

生成物 1

HCID 86606015(1R,2S,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzylsulfinyl)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester収率 83.5%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane
溶媒

実験手順

32 mg of 3-chloroperbenzoic acid was added to 73 mg of (1R,2S,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzylsulfanyl)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester dissolved in 1.46 mL of dichloromethane and the mixture was stirred for 1 hour in a dry ice-acetone bath. The mixture was stirred for 3.5 hours in an ice bath, and further stirred for 11 hours at room temperature. 15 mg of 3-chloroperbenzoic acid was further added thereto, and the mixture was stirred for 1 hour in a dry ice-acetone bath, and then stirred for 4 hours in an ice bath. The reaction solution was washed with a saturated aqueous solution of sodium hydrogen carbonate and with a saturated aqueous solution of sodium chloride, and then dried over anhydrous sodium sulfate. The desiccant was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by column chromatography (silica gel: Wako gel C200 (made by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=4:1 to 2:1), thereby yielding 63 mg of (1R,2S,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzylsulfinyl)-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester and 12 mg of (1R,2S,3R,5R,6R)-2-azido-3-(3,4-dichlorobenzylsulfonyl-6-fluoro-bicyclo[3.1.0]hexane-2,6-dicarboxylic acid diethyl ester.

後処理

  1. stirringThe mixture was stirred for 3.5 hours in an ice bath
  2. stirringfurther stirred for 11 hours at room temperature
  3. stirringthe mixture was stirred for 1 hour in a dry ice-acetone bath
  4. stirringstirred for 4 hours in an ice bath
  5. washThe reaction solution was washed with a saturated aqueous solution of sodium hydrogen carbonate and with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous sodium sulfate
  7. filtrationThe desiccant was filtered off
  8. concentrationthe filtrate was concentrated under reduced pressure
  9. customThe residue was purified by column chromatography (silica gel: Wako gel C200 (made by Wako Pure Chemical Industries Ltd.), eluent: hexane-ethyl acetate=4:1 to 2:1)

出典と根拠

ORDレコード
ord-7007f06c0471475a98e70969cfd22741
出典データセット
uspto-grants-2008_06
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07381746B2

反応ノート

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