Hydrochloric Acid → 3-Ethoxy-3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid

HRID 1747338Notes

Reaction equation

HRID 1747338 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][CH:6]([O:28][CH2:29][CH3:30])[N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([CH2:16][C:17]2[C:18]3[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:19]=3[S:20][CH:21]=2)[C:8]1=[O:27])C.[OH-].[Na+].Cl.O>CO>[CH2:29]([O:28][CH:6]([N:7]1[C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][C:10]=2[N:9]([CH2:16][C:17]2[C:18]3[C:25]([CH3:26])=[CH:24][CH:23]=[CH:22][C:19]=3[S:20][CH:21]=2)[C:8]1=[O:27])[CH2:5][C:4]([OH:31])=[O:3])[CH3:30]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 594973143-Ethoxy-3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid ethyl ester

Product 1

HCID 251278473-Ethoxy-3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acidYield 99.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-Ethoxy-3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid ethyl ester (50 mg, 0.11 mmol) in MeOH (3.0 mL) is added 2.0 N NaOH solution (1.0 mL). The reaction mixture is stirred at room temperature for 2 h. Then 1.0 M HCl solution (3.0 mL) and water (10 mL) are added and the reaction mixture is extracted with EtOAc (3×20 mL). The organic layers are combined, dried and concentrated to give 45 mg (96%) of the crude 3-Ethoxy-3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid which is used in the next step without further purification.

Workup

  1. extractionthe reaction mixture is extracted with EtOAc (3×20 mL)
  2. customdried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-8afe07df5c1d4af38d65616526bfe4f7
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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