Sodium Hydroxide → HCID 58968947, compound

HRID 545470Notes

Reaction equation

HRID 545470 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[CH:12]=[C:11]([C:13](=[O:35])[NH:14][O:15][C:16]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[S:10][C:9]=2[CH:36]=1)=[O:4].[OH-].[Na+]>C1COCC1.CO.CCOC(C)=O.O>[C:16]([O:15][NH:14][C:13]([C:11]1[S:10][C:9]2[CH:36]=[C:5]([C:3]([OH:4])=[O:2])[CH:6]=[CH:7][C:8]=2[CH:12]=1)=[O:35])([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1

Participants

6

Reactant 2

HCID 14798Sodium Hydroxide3×HCID 58969051HCID 58969051, compound

Product 1

HCID 58968947HCID 58968947, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8857Ethyl AcetateSolventHCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 2-trityloxycarbamoyl-benzo[b]thiophene-6-carboxylic acid methyl ester (4.12 g, 8.35 mmol) in THF/MeOH (50/10 mL) was added 2 N NaOH (16 mL). After 1.5 h, added an additional 5 mL of 3 N NaOH. After another 1 h, added an additional 16 mL of 2 N NaOH, and stirred overnight. The solution was diluted with EtOAc (100 mL) and H2O (100 mL) and washed with EtOAc. The aqueous fractions were acidified with 5% citric acid, and extracted with EtOAc. The combined organic fractions were dried, filtered, and concentrated to yield the desired acid, which was used without further purification. MS (EI): cal'd (M−), 478.1, exp (M−), 478.6.

Workup

  1. waitAfter another 1 h
  2. washwashed with EtOAc
  3. extractionextracted with EtOAc
  4. customThe combined organic fractions were dried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-d1f00440d70a439485aa431f0833fbe1
Source dataset
uspto-grants-2011_05
Patent number
US07935724B2

Reaction notes

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