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Phosgene → 4-(4-Acryloylamino-benzenesulfonyl)-piperazine-1-carboxylic acid 2-chloro-benzyl ester

HRID 1841924
ノート
印刷プレビュー

反応式

HRID 1841924 の反応式
[C:1](Cl)(Cl)=[O:2].[Cl:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH2:8][OH:9].[N:14]1([S:20]([C:23]2[CH:28]=[CH:27][C:26]([NH:29][C:30](=[O:33])[CH:31]=[CH2:32])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH2:19][CH2:18][NH:17][CH2:16][CH2:15]1.C(N(C(C)C)CC)(C)C>C1COCC1.CN(C=O)C>[Cl:5][C:6]1[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=1[CH2:8][O:9][C:1]([N:17]1[CH2:16][CH2:15][N:14]([S:20]([C:23]2[CH:24]=[CH:25][C:26]([NH:29][C:30](=[O:33])[CH:31]=[CH2:32])=[CH:27][CH:28]=2)(=[O:21])=[O:22])[CH2:19][CH2:18]1)=[O:2]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 6371PhosgeneHCID 288102-Chlorobenzyl alcoholHCID 81531DiisopropylethylamineHCID 56953730N-[4-(piperazine-1-sulfonyl)-phenyl]-acrylamide

生成物 1

HCID 529396444-(4-Acryloylamino-benzenesulfonyl)-piperazine-1-carboxylic acid 2-chloro-benzyl ester収率 12%

試薬・触媒・溶媒 2

HCID 6228
Dimethylformamide
溶媒
HCID 8028Tetrahydrofuran溶媒

実験手順

Phosgene (0.5 ml, 20% solution in toluene) was added in one portion to a stirred solution of 2-chlorobenzyl alcohol (0.1 g, 0.7 mmol) in THF (2 ml) and the resulting mixture was stirred at room temperature under a nitrogen atmosphere for 3 hours. After this time the reaction mixture was concentrated under vacuum and the resulting residue was diluted with DMF (2 ml) and added drop wise to a stirred solution of N-[4-(piperazine-1-sulfonyl)-phenyl]-acrylamide (0.16 g, 0.54 mmol) and diisopropylethylamine (0.19 ml, 1.1 mmol) in DMF (4 ml). The resulting mixture was stirred at room temperature under a nitrogen atmosphere for 18 hours. After this time the reaction mixture was concentrated under vacuum and the residue was purified by Prep HPLC to give the title compound (0.029 g, 12% yield) as a white powder.

後処理

  1. concentrationAfter this time the reaction mixture was concentrated under vacuum
  2. additionthe resulting residue was diluted with DMF (2 ml)
  3. stirringThe resulting mixture was stirred at room temperature under a nitrogen atmosphere for 18 hours
  4. concentrationAfter this time the reaction mixture was concentrated under vacuum
  5. customthe residue was purified by Prep HPLC

出典と根拠

ORDレコード
ord-852b23af1f314c938a12cbf4ce4c30bc
出典データセット
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08946197B2

反応ノート

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