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

HRID 1747335Notes

Reaction equation

HRID 1747335 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:34])[CH2:7][CH:8]([N:13]1[C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=2[N:15]([CH2:22][C:23]2[C:24]3[C:31]([CH3:32])=[CH:30][CH:29]=[CH:28][C:25]=3[S:26][CH:27]=2)[C:14]1=[O:33])[CH2:9][C:10]([OH:12])=[O:11].Cl>O.CO>[CH3:32][C:31]1[C:24]2[C:23]([CH2:22][N:15]3[C:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=4[N:13]([CH:8]([CH2:9][C:10]([OH:12])=[O:11])[CH2:7][C:6]([OH:34])=[O:5])[C:14]3=[O:33])=[CH:27][S:26][C:25]=2[CH:28]=[CH:29][CH:30]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 251235483-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanedioic acid monomethyl ester

Product 1

HCID 251238813-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanedioic acidYield 87%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent2×

Procedure

Lithium hydroxide monohydrate (7.2 mg, 0.17 mmol) is dissolved in water (1.0 mL) and it is added into the solution of 3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanedioic acid monomethyl ester (25 mg, 0.057 mmol) in methanol (1.0 mL) at room temperature. The mixture is stirred for 2 hr and then 1.0 M HCl solution (0.5 mL) is added along with water (10 mL). The mixture is extracted with EtOAc (3×10 mL) and the organic layers are combined, dried over MgSO4 and concentrated to give crude product. Purification by preparative TLC using 5% MeOH in CH2Cl2 with 1% acetic acid afforded 21 mg (87%) of 3-[3-(4-Methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-pentanedioic acid. LCMS (ESMS): m/z 425.22 (M+H+).

Workup

  1. extractionThe mixture is extracted with EtOAc (3×10 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated
  4. customto give crude product
  5. customPurification by preparative TLC

Sources & evidence

ORD record
ord-25de9e78562d4be58bbe494549608c1a
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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