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

HRID 1747329Notes

Reaction equation

HRID 1747329 reaction equation
C([O:3][C:4](=[O:31])[CH2:5][CH:6]([N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]([CH2:19][C:20]2[C:21]3[C:28]([CH3:29])=[CH:27][CH:26]=[CH:25][C:22]=3[S:23][CH:24]=2)[C:11]1=[O:30])[CH2:7][CH2:8][CH3:9])C.[OH-].[Na+].Cl.O>CO>[CH3:29][C:28]1[C:21]2[C:20]([CH2:19][N:12]3[C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=4[N:10]([CH:6]([CH2:7][CH2:8][CH3:9])[CH2:5][C:4]([OH:31])=[O:3])[C:11]3=[O:30])=[CH:24][S:23][C:22]=2[CH:25]=[CH:26][CH:27]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 594976173-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester

Product 1

HCID 251281763-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester (65 mg, 0.15 mmol) in MeOH (3.0 mL) is added 2.0 N NaOH (0.5 mL). The reaction mixture is stirred at room temperature for 3.5 h and then 1.0M HCl (1.5 mL) and water (50 mL) are added. The mixture is extracted with EtOAc (3×50 mL). The organic layers are combined, dried over MgSO4 and concentrated to give crude product. Purification by flash column chromatography affords 56 mg (92%) of 3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid.

Workup

  1. extractionThe mixture is extracted with EtOAc (3×50 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customto give crude product
  5. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-ac0025693d8d4a3583a7d982149a1ee1
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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