Citric Acid → HCID 69489781, 화합물

HRID 1271862노트

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HRID 1271862 반응식
[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[S:21][C:20]2[CH:22]=[CH:23][C:24]([OH:26])=[CH:25][C:19]=2[CH:18]=1)=[O:16])([CH3:4])([CH3:3])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Br[CH2:35][CH2:36][O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>C(#N)C>[C:1]([O:5][C:6](=[O:27])[NH:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:14][C:15]([C:17]1[S:21][C:20]2[CH:22]=[CH:23][C:24]([O:26][CH2:35][CH2:36][O:37][Si:38]([C:41]([CH3:44])([CH3:43])[CH3:42])([CH3:40])[CH3:39])=[CH:25][C:19]=2[CH:18]=1)=[O:16])([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 69487009HCID 69487009, 화합물

생성물 1

HCID 69489781HCID 69489781, 화합물

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
85 °C

실험 절차

To a solution of 96 mg (0.25 mmol) {2-[(5-Hydroxy-benzo[b]thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester (4) in 5 ml acetonitrile was added 120 mg potassium carbonate and 0.3 ml (2-bromoethoxy)-tert-butyldimethylsilane. The reaction mixture was heated at reflux for 90 min and at 85° C. for 2 h and poured into 5% aqueous citric acid. The aqueous phase was extracted with ethyl acetate and the organic phase was dried over sodium sulfate, the solvent was evaporated and the residue subjected to silica gel chromatography (petrolether/ethylacetate 4:1 and then 9:1). [2-({5-[2-(tert-Butyl-dimethyl-silanyloxy)-ethoxy]-benzo[b]thiophene-2-carbonyl}-amino)-phenyl]-carbamic acid tert-butyl ester (40) (63 mg, 0.116 mmol) was obtained as a colorless solid.

후처리

  1. temperatureThe reaction mixture was heated
  2. extractionThe aqueous phase was extracted with ethyl acetate
  3. dry with materialthe organic phase was dried over sodium sulfate
  4. customthe solvent was evaporated

출처 및 근거

ORD 기록
ord-0c3aa16f2d9e4675aa2cc9484e28d123
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07208491B2

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