Hydrochloric Acid → HCID 25126219, compound

HRID 1747296Notes

Reaction equation

HRID 1747296 reaction equation
C([O:3][C:4](=[O:32])[CH2:5][C@@H:6]([N:10]1[C:14]2[CH:15]=[C:16]([CH3:19])[CH:17]=[CH:18][C:13]=2[N:12]([CH2:20][C:21]2[C:22]3[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][C:23]=3[S:24][CH:25]=2)[C:11]1=[O:31])[CH2:7][CH2:8][CH3:9])C.[OH-].[Na+].Cl>CO>[CH3:19][C:16]1[CH:17]=[CH:18][C:13]2[N:12]([CH2:20][C:21]3[C:22]4[C:29]([CH3:30])=[CH:28][CH:27]=[CH:26][C:23]=4[S:24][CH:25]=3)[C:11](=[O:31])[N:10]([C@@H:6]([CH2:7][CH2:8][C:9]3[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=3)[CH2:5][C:4]([OH:3])=[O:32])[C:14]=2[CH:15]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67360619HCID 67360619, compound

Product 1

HCID 25126219HCID 25126219, compoundYield 179.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (S)-3-[6-Methyl-3-(4-methyl-benzo[b]thiophen-3-ylmethyl)-2-oxo-2,3-dihydro-benzimidazol-1-yl]-hexanoic acid ethyl ester (0.12 g, 0.23 mmol) in MeOH (5 mL) was added 2N NaOH (2 mL). The reaction mixture was stirred at room temperature for 2 h. When the reaction was complete, the reaction mixture was treated with 1N HCl and extracted with CH2Cl2 (×2). The organic phase was dried over Na2SO4 and concentrated. The resulting residue was purified by silica gel prep TLC using 10:1 CH2Cl2:MeOH as an eluent to afford 0.1 g of the title compound as a white solid. LCMS (ESMS): m/z 485.54 (M+H+).

Workup

  1. extractionextracted with CH2Cl2 (×2)
  2. dry with materialThe organic phase was dried over Na2SO4
  3. concentrationconcentrated
  4. customThe resulting residue was purified by silica gel prep TLC

Sources & evidence

ORD record
ord-5eb1042451b1422b895714d814566cf2
Source dataset
uspto-grants-2015_10
Patent number
US09150556B2

Reaction notes

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