Citric Acid → HCID 69489781、化合物

HRID 1271862ノート

反応式

HRID 1271862 の反応式
[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]

参加物

6

反応物 4

HCID 311Citric AcidHCID 11430Potassium CarbonateHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 69487009HCID 69487009、化合物

生成物 1

HCID 69489781HCID 69489781、化合物

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
85 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0c3aa16f2d9e4675aa2cc9484e28d123
出典データセット
uspto-grants-2007_04
特許番号
US07208491B2

反応ノート

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