2-Trityloxycarbamoyl-benzo[b]thiophene-5-carboxylic acid methyl ester → 2-Trityloxycarbamoyl-benzo[b]thiophene-5-carboxylic acid

HRID 545477Notes

Reaction equation

HRID 545477 reaction equation
C[O:2][C:3]([C:5]1[CH:36]=[CH:35][C:8]2[S:9][C:10]([C:12](=[O:34])[NH:13][O:14][C:15]([C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[CH:11][C:7]=2[CH:6]=1)=[O:4]>C1COCC1.[OH-].[Na+]>[C:15]([O:14][NH:13][C:12]([C:10]1[S:9][C:8]2[CH:35]=[CH:36][C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=2[CH:11]=1)=[O:34])([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:28]1[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=1

Participants

4

Reactant 1

HCID 866150442-Trityloxycarbamoyl-benzo[b]thiophene-5-carboxylic acid methyl ester

Product 1

HCID 866150452-Trityloxycarbamoyl-benzo[b]thiophene-5-carboxylic acid

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 2-trityloxycarbamoyl -benzo[b]thiophene-5-carboxylic acid methyl ester (4.439 g, 8.99 mmol) in THF (50 mL) and 2M aqueous NaOH (50 mL) was allowed to stir at rt for six days. After removal of THF, the aqueous phase was acidified with HOAc/H2O (1:1) to pH≈4. The solid formed was filtered, collected and dried to give 2-trityloxycarbamoyl-benzo[b]thiophene-5-carboxylic acid as a white solid. 1H NMR (DMSO-d6, 200 MHz) δ 11.33 (brs, 1H), 8.47 (s, 1H), 8.10-7.80 (m, 3H), 7.56-7.14 (m, 15H). MS (EI): cal'd 243.1 (M-benzothiophene moiety+H+,) exp 243.1 (M-benzothiophene moiety+H+).

Workup

  1. customAfter removal of THF
  2. customThe solid formed
  3. filtrationwas filtered
  4. customcollected
  5. customdried

Sources & evidence

ORD record
ord-a0893e0cf7fe47fbaed278161e72809b
Source dataset
uspto-grants-2011_05
Patent number
US07935724B2

Reaction notes

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