Toluene → 1-{(2-Ethoxycarbonylvinyl)-[4-(4-fluorophenoxy) benzenesulfonyl]-amino}cyclopentanecarboxylic Acid Benzyl Ester

HRID 1596003ノート

反応式

HRID 1596003 の反応式
[CH2:1]([O:8][C:9]([C:11]1([NH:16][S:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:34]([O:38][CH2:39][CH3:40])(=[O:37])[C:35]#[CH:36].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C1(C)C=CC=CC=1>O1CCCC1>[CH2:1]([O:8][C:9]([C:11]1([N:16]([CH:36]=[CH:35][C:34]([O:38][CH2:39][CH3:40])=[O:37])[S:17]([C:20]2[CH:25]=[CH:24][C:23]([O:26][C:27]3[CH:32]=[CH:31][C:30]([F:33])=[CH:29][CH:28]=3)=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:15][CH2:14][CH2:13][CH2:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 4

HCID 1140TolueneHCID 12182Ethyl propiolateHCID 2724141Tetrabutylammonium FluorideHCID 110051711-[4-(4-Fluorophenoxy)benzenesulfonylamino]-cyclopentanecarboxylic acid benzyl ester

生成物 1

HCID 543914121-{(2-Ethoxycarbonylvinyl)-[4-(4-fluorophenoxy) benzenesulfonyl]-amino}cyclopentanecarboxylic Acid Benzyl Ester

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒3 回

実験手順

A solution of 25.0 g (532 mmol) of 1-[4-(4-fluorophenoxy)benzenesulfonylamino]cyclopentane-carboxylic acid benzyl ester and 10.8 mL (106 mmol, 2 equivalents) of ethyl propiolate in 200 mL of dry tetrahydrofuran at 1° C. was treated with 53.2 mL (53.2 mmol, 1 equivalent) of a solution of tetrabutylammonium fluoride in tetrahydrofuran (1M) over 45 minutes. The resulting solution was allowed to warm slowly to ambient temperature and stirred overnight, The tetrahydrofuran was displaced with toluene at reduced pressure, and the toluene solution was washed with water and brine, diluted to 600 mL with toluene, stirred with 90 g of silica gel for three hours, filtered, and concentrated to 25.14 g (83%) of 1-{(2-ethoxycarbonyivinyl)-[4-(4-fluorophenoxy)benzenesulfonyl]amino}-cyclopentanecarboxylic acid benzyl ester as an orangea oil. 1H NMR (CDCl3) indicated a 1.5:1 translcis ratio.

後処理

  1. washthe toluene solution was washed with water and brine
  2. additiondiluted to 600 mL with toluene
  3. stirringstirred with 90 g of silica gel for three hours
  4. filtrationfiltered
  5. concentrationconcentrated to 25.14 g (83%) of 1-{(2-ethoxycarbonyivinyl)-[4-(4-fluorophenoxy)benzenesulfonyl]amino}-cyclopentanecarboxylic acid benzyl ester as an orangea oil

出典と根拠

ORDレコード
ord-2ffc025b178644c6ab8f4ba02e541815
出典データセット
uspto-grants-2001_09
特許番号
US06288246B1

反応ノート

読み込み中…