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Imidazol-1-YL-oxo-acetic acid tert-butyl ester → 2-(tert-butyoxyoxalyl-amino)-5-((2-(1H-indol-3-yl)-2-oxo-acetylamino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester

HRID 2188022
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HRID 2188022 반응식
[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][CH:14]([CH2:17][NH:18][C:19](=[O:31])[C:20]([C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][CH:23]=3)=[O:21])[N:13]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=3)[CH2:12][C:11]=2[S:10][C:9]=1[NH2:41])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:42]([O:46][C:47](=[O:55])[C:48](N1C=CN=C1)=[O:49])([CH3:45])([CH3:44])[CH3:43]>ClCCl>[C:1]([O:5][C:6]([C:8]1[C:16]2[CH2:15][CH:14]([CH2:17][NH:18][C:19](=[O:31])[C:20]([C:22]3[C:30]4[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=4)[NH:24][CH:23]=3)=[O:21])[N:13]([CH2:32][C:33]3[CH:38]=[CH:37][C:36]([O:39][CH3:40])=[CH:35][CH:34]=3)[CH2:12][C:11]=2[S:10][C:9]=1[NH:41][C:48](=[O:49])[C:47]([O:46][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:55])=[O:7])([CH3:4])([CH3:3])[CH3:2]
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참가 물질

4

반응물 2

HCID 11217804Imidazol-1-YL-oxo-acetic acid tert-butyl ester2회HCID 695860462-amino-5-((2-(1H-indol-3-yl)-2-oxo-acetylamino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester

생성물 1

HCID 1317233162-(tert-butyoxyoxalyl-amino)-5-((2-(1H-indol-3-yl)-2-oxo-acetylamino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester수율 58%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a solution of 2-amino-5-((2-(1H-indol-3-yl)-2-oxo-acetylamino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester (143 mg, 0.25 mmol) in dichloromethane (5 ml) was added imidazol-1-yl-oxo-acetic acid tert-butyl ester (144 mg, 0.75 mmol) and the flask was purged with nitrogen. After 24 hours an additional portion of imidazol-1-yl-oxo-acetic acid tert-butyl ester (169 mg, 0.86 mmol) was added and the reaction mixture allowed stirred for an additional 24 hours. The mixture was then concentrated in vacuo. The residue was purified by flash chromatography using a mixture of ethyl acetate/hexanes (2:5) as eluent, which afforded 101 mg (58%) of 2-(tert-butyoxyoxalyl-amino)-5-((2-(1H-indol-3-yl)-2-oxo-acetylamino)methyl)-6-(4-methoxy-benzyl)-4,5,6,7-tetrahydro-thieno[2,3-c]pyridine-3-carboxylic acid tert-butyl ester as a oil.

후처리

  1. customthe flask was purged with nitrogen
  2. concentrationThe mixture was then concentrated in vacuo
  3. customThe residue was purified by flash chromatography
  4. additiona mixture of ethyl acetate/hexanes (2:5) as eluent

출처 및 근거

ORD 기록
ord-c551a959fb104b3b90f6a44ce731aebf
출처 데이터셋
uspto-grants-2002_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06410556B1

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