Dicyclohexylcarbodiimide → benzoylmercaptoacetyl-N-hydroxysuccinimide

HRID 342334

反応式

HRID 342334 の反応式
[C:1]([S:9][CH2:10][C:11]([OH:13])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH:14][N:15]1[C:19](=[O:20])[CH2:18][CH2:17][C:16]1=[O:21].C1(N=C=NC2CCCCC2)CCCCC1>O1CCOCC1>[C:1]([S:9][CH2:10][C:11]([CH:17]1[CH2:18][C:19](=[O:20])[N:15]([OH:14])[C:16]1=[O:21])=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

5

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 80170N-HydroxysuccinimideHCID 51165332-benzoylsulfanylacetic Acid

生成物 1

HCID 86749986benzoylmercaptoacetyl-N-hydroxysuccinimide収率 78.5%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒2 回

反応条件

温度
4 °C

実験手順

To a stirring solution of (9.20 g, 46.9 mmoles) benzoylmercaptoacetic acid and (5.41 g, 46.9 mmoles) N-hydroxysuccinimide in (100 mL) dioxane was added a solution of (9.70 g, 47 mmoles) dicyclohexylcarbodiimide in (40 mL) dioxane. The reaction was stirred 12 hours followed by cooling to 4° C., filtering, and rotavapping off the dioxane to a white solid. The solid was triturated with cold isopropanol, filtered, and dried in vacuo yielding 10.8 g, 78% benzoylmercaptoacetyl-N-hydroxysuccinimide. 200 mg was recrystallized from 500 mg in hot ethyl acetate.

後処理

  1. filtrationfiltering
  2. customThe solid was triturated with cold isopropanol
  3. filtrationfiltered
  4. customdried in vacuo

出典と根拠

ORDレコード
ord-80b20cf679f04c699d08db924326939d
出典データセット
uspto-grants-1999_01
特許番号
US05858327

関連ノート

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