Potassium Carbonate → HCID 69489700, compound

HRID 1271866Notes

Reaction equation

HRID 1271866 reaction equation
[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+].Cl[CH2:35][C:36]([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37].[Cl-].[NH4+]>C(OCC)(=O)C>[C:39]([O:38][C:36](=[O:37])[CH2:35][O:26][C:24]1[CH:23]=[CH:22][C:20]2[S:21][C:17]([C:15](=[O:16])[NH:14][C:9]3[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=3[NH:7][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:27])=[CH:18][C:19]=2[CH:25]=1)([CH3:42])([CH3:41])[CH3:40]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 66052tert-Butyl chloroacetateHCID 69487009HCID 69487009, compound

Product 1

HCID 69489700HCID 69489700, compoundYield 45.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

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 3 ml ethyl acetate was added 140 mg potassium carbonate and 60 mg (0.40 mmol) tert-butyl chloroacetate. The reaction mixture was heated at reflux for 16 h and poured into a saturated aqueous solution of ammonium chloride. 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/ethyl acetate 4:1). The product fraction was recrystallized from heptane/diethylether to yield 57 mg (0.114 mmol) [2-(2-tert-Butoxycarbonylamino-phenylcarbamoyl)-benzo[b]thiophen-5-yloxy]-acetic acid tert-butyl ester (46), mp. 166° C.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureat reflux for 16 h
  3. extractionThe aqueous phase was extracted with ethyl acetate
  4. dry with materialthe organic phase was dried over sodium sulfate
  5. customthe solvent was evaporated
  6. customThe product fraction was recrystallized from heptane/diethylether

Sources & evidence

ORD record
ord-d6fe7d8028ec46aa83fd9be1a9969c32
Source dataset
uspto-grants-2007_04
Patent number
US07208491B2

Reaction notes

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