Citric Acid → HCID 69487009, compound

HRID 1271844Notes

Reaction equation

HRID 1271844 reaction equation
[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]

Participants

5

Reactant 3

HCID 311Citric AcidHCID 10942334Sodium MethoxideHCID 86760485HCID 86760485, compound

Product 1

HCID 69487009HCID 69487009, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

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.).

Workup

  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.)

Sources & evidence

ORD record
ord-71b8f13f79894337a342dfe59a1ba393
Source dataset
uspto-grants-2007_04
Patent number
US07208491B2

Reaction notes

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