3-Nitrobenzenesulfonyl chloride → (2S,4R)-4-(3-Nitro-benzenesulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

HRID 38042

反応式

HRID 38042 の反応式
[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([OH:10])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4].[N+:18]([C:21]1[CH:22]=[C:23]([S:27](Cl)(=[O:29])=[O:28])[CH:24]=[CH:25][CH:26]=1)([O-:20])=[O:19]>C(Cl)Cl>[CH3:1][O:2][C:3]([C@@H:5]1[CH2:9][C@@H:8]([O:10][S:27]([C:23]2[CH:24]=[CH:25][CH:26]=[C:21]([N+:18]([O-:20])=[O:19])[CH:22]=2)(=[O:28])=[O:29])[CH2:7][N:6]1[C:11]([O:13][C:14]([CH3:17])([CH3:16])[CH3:15])=[O:12])=[O:4]

参加物

4

反応物 2

HCID 84763-Nitrobenzenesulfonyl chlorideHCID 2734883(2S,4R)-4-Hydroxypyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester

生成物 1

HCID 86664754(2S,4R)-4-(3-Nitro-benzenesulfonyloxy)-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester収率 103.1%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
5 °C

実験手順

(2S,4R)-4-Hydroxy-pyrrolidine-1,2-dicarboxylic acid 1-tert-butyl ester 2-methyl ester (5.0 g) was dissolved in DCM (50 mL) and 3-nitrobenzenesulfonyl chloride (4.8 g) was added. This solution was cooled to 5° C. and the TEA (8.52 mL) was carefully added. The reaction mixture was stirred at 25° C. for 18 h. The reaction mixture was then extracted with 0.1 N aqueous HCl (50 mL) and aqueous Na2CO3 (50 mL) and brine (50 mL). The organic layer was dried over Na2SO4, filtrated and evaporated to dryness to yield a light brown amorphous solid (9.05 g). MS: m/z=431.4 [M+H]+.

後処理

  1. extractionThe reaction mixture was then extracted with 0.1 N aqueous HCl (50 mL) and aqueous Na2CO3 (50 mL) and brine (50 mL)
  2. dry with materialThe organic layer was dried over Na2SO4
  3. filtrationfiltrated
  4. customevaporated to dryness

出典と根拠

ORDレコード
ord-ed6f79568ea1451898ce3a8046113a50
出典データセット
uspto-grants-2013_09
特許番号
US08524710B2

関連ノート

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