Hydrochloric Acid → 6-(Carbamoyl-fluoro-methyl)benzo[b]thiophene-2-carboxylic acid

HRID 1172898Notes

Reaction equation

HRID 1172898 reaction equation
C([O:3][C:4]([C:6]1[S:10][C:9]2[CH:11]=[C:12]([CH:15]([C:17](=[O:19])[NH2:18])[F:16])[CH:13]=[CH:14][C:8]=2[CH:7]=1)=[O:5])C.[Li+].[OH-].Cl>CO.C1COCC1>[C:17]([CH:15]([F:16])[C:12]1[CH:13]=[CH:14][C:8]2[CH:7]=[C:6]([C:4]([OH:5])=[O:3])[S:10][C:9]=2[CH:11]=1)(=[O:19])[NH2:18]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 595564086-(Carbamoyl-fluoro-methyl)-benzo[b]thiophene-2-carboxylic acid ethyl ester

Product 1

HCID 595564146-(Carbamoyl-fluoro-methyl)benzo[b]thiophene-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of 6-(carbamoyl-fluoro-methyl)-benzo[b]thiophene-2-carboxylic acid ethyl ester (295 mg, 1.05 mmol) in MeOH/THF (1.5/6 mL) was added 1M LiOH (1.16 mL). The resultant solution was stirred overnight and 1N HCl was added dropwise to acidify (˜2 mL). The solvent was removed in vacuo and the solid was used without further purification. cal'd 254 (MH+), exp 254 (MH+).

Workup

  1. customThe solvent was removed in vacuo
  2. customthe solid was used without further purification

Sources & evidence

ORD record
ord-39a5a77b3c6741fb9f3060019c48440c
Source dataset
uspto-grants-2010_11
Patent number
US07834034B2

Reaction notes

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