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

HRID 1747327Notes

Reaction equation

HRID 1747327 reaction equation
O.[OH-].[Li+].C[O:5][C:6](=[O:32])[C:7]([CH3:31])([CH3:30])[CH2:8][N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([CH2:18][C:19]2[C:20]3[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:21]=3[S:22][CH:23]=2)[C:10]1=[O:29].Cl>O.O1CCOCC1>[CH3:30][C:7]([CH3:31])([CH2:8][N:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]([CH2:18][C:19]2[C:20]3[C:27]([CH3:28])=[CH:26][CH:25]=[CH:24][C:21]=3[S:22][CH:23]=2)[C:10]1=[O:29])[C:6]([OH:32])=[O:5]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 168937Lithium hydroxide, monohydrateHCID 594976752,2-Dimethyl-3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid methyl ester

Product 1

HCID 251258942,2-Dimethyl-3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]propionic acidYield 91.8%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Procedure

Lithium hydroxide monohydrate (4.3 mg, 0.10 mmol) is dissolved in water (1.0 mL) and it is added into the solution of 2,2-Dimethyl-3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-propionic acid methyl ester (28 mg, 0.069 mmol) in 1,4-dioxane (2.0 mL) at room temperature. The mixture is stirred for 60 hr and LCMS then 1.0 M HCl solution (1.0 mL) is added followed by water (15 mL). Then the mixture is extracted with EtOAc (3×30 mL) and the organic layers are combined, dried over MgSO4 and concentrated to give 25 mg (90%) of 2,2-Dimethyl-3-[3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3dihydro-benzimidazol-1-yl]propionic acid. LCMS (ESMS): m/z 395.17 (M+H+).

Workup

  1. extractionThen the mixture is extracted with EtOAc (3×30 mL)
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-e634585f9d1744fea0a0a3bd440a48ea
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

Loading…