Citric Acid → HCID 69487009、化合物

HRID 1271844ノート

反応式

HRID 1271844 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]([C:18]1[S:22][C:21]2[CH:23]=[CH:24][C:25]([O:27]C(=O)C3C=CC=CC=3)=[CH:26][C:20]=2[CH:19]=1)=[O:17])=[O:7])([CH3:4])([CH3:3])[CH3:2].C[O-].[Na+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CO>[C:1]([O:5][C:6](=[O:7])[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[NH:15][C:16]([C:18]1[S:22][C:21]2[CH:23]=[CH:24][C:25]([OH:27])=[CH:26][C:20]=2[CH:19]=1)=[O:17])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 311Citric AcidHCID 10942334Sodium MethoxideHCID 86760485HCID 86760485、化合物

生成物 1

HCID 69487009HCID 69487009、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

To a suspension of 732 mg (1.5 mmol) benzoic acid 2-(2-tert-butoxycarbonylamino-phenylcarbamoyl)-benzo[b]thiophen-5-yl ester (3) in 30 ml methanol was added 1.0 ml of a 5.4M solution of NaOMe in methanol. After 3 h at room temperature the reaction solution was poured on 5% aqueous citric acid. Extraction with ethyl acetate, washing of the organic phase with brine. The organic phase was dried over sodium sulfate, the solvent was evaporated and the residue subjected to silica gel chromatography (petrolether/ethyl acetate 3:1). {2-[(5-Hydroxy-benzo[b]thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester (4) was recrystallized from ethyl acetate/diethyl ether to yield 546 mg (1.42 mmol) as colorless crystals, mp. 185° C. (decomp.).

後処理

  1. extractionExtraction with ethyl acetate
  2. washwashing of the organic phase with brine
  3. dry with materialThe organic phase was dried over sodium sulfate
  4. customthe solvent was evaporated
  5. custom{2-[(5-Hydroxy-benzo[b]thiophene-2-carbonyl)-amino]-phenyl}-carbamic acid tert-butyl ester (4) was recrystallized from ethyl acetate/diethyl ether
  6. customto yield 546 mg (1.42 mmol) as colorless crystals, mp. 185° C. (decomp.)

出典と根拠

ORDレコード
ord-71b8f13f79894337a342dfe59a1ba393
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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