Sodium Bicarbonate → HCID 10362721, compound

HRID 1271856Notes

Reaction equation

HRID 1271856 reaction equation
C(OC(=O)[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][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33])=[CH:25][C:19]=2[CH:18]=1)=[O:16])(C)(C)C.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O>[NH2:7][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][CH2:27][CH2:28][O:29][CH2:30][CH2:31][O:32][CH3:33])=[CH:25][C:19]=2[CH:18]=1)=[O:16]

Participants

4

Reactant 2

HCID 516892Sodium BicarbonateHCID 86593875HCID 86593875, compound

Product 1

HCID 10362721HCID 10362721, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 80 mg (0.164 mmol) of [2-({5-[2-(2-Methoxy-ethoxy)-ethoxy]-benzo[b]thiophene-2-carbonyl}-amino)-phenyl]-carbamic acid tert-butyl ester (28) in 1.0 ml trifluoroacetic acid was stirred for 45 min at room temperature and then added to an aqueous solution of sodium bicarbonate. After extraction with ethyl acetate and removal of the solvent the residue was recrystallized from ethyl acetate/heptane to yield 40 mg (0.103 mmol) of the desired product (27) as white crystals, mp. 167–168° C.

Workup

  1. extractionAfter extraction
  2. customwith ethyl acetate and removal of the solvent the residue
  3. customwas recrystallized from ethyl acetate/heptane

Sources & evidence

ORD record
ord-dca74ae1eaf148c1ae454ec44ad3f05b
Source dataset
uspto-grants-2007_04
Patent number
US07208491B2

Reaction notes

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