Methanol → 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}pyrrolidine-3-carboxylic acid

HRID 1435494Notes

Reaction equation

HRID 1435494 reaction equation
[OH-].[Na+].[C:3]([C:7]1[N:11]([CH2:12][CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:10]2[CH:19]=[CH:20][C:21]([S:23]([N:26]3[CH2:30][CH2:29][CH:28]([C:31]([O:33]C)=[O:32])[CH2:27]3)(=[O:25])=[O:24])=[CH:22][C:9]=2[N:8]=1)([CH3:6])([CH3:5])[CH3:4].CO>O>[C:3]([C:7]1[N:11]([CH2:12][CH:13]2[CH2:14][CH2:15][O:16][CH2:17][CH2:18]2)[C:10]2[CH:19]=[CH:20][C:21]([S:23]([N:26]3[CH2:30][CH2:29][CH:28]([C:31]([OH:33])=[O:32])[CH2:27]3)(=[O:25])=[O:24])=[CH:22][C:9]=2[N:8]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 57937292HCID 57937292, compound

Product 1

HCID 579373041-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}pyrrolidine-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

NaOH (2 mL, 2 M, 4.0 mmol) was added to a solution of methyl 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}pyrrolidine-3-carboxylate (570 mg, 1.22 mmol) in a 1:1 mixture of MeOH:H2O (30 mL) at ambient temperature. The reaction mixture was stirred overnight and diluted with water (100 mL). The solvent was concentrated to 100 mL. The resulting solution was neutralized with HCl solution, the product was extracted with EtOAc and dried over anhydrous Na2SO4. The solvent was concentrated to provide the title compound as white solid. Yield: 480 mg (87%); MS (ESI) (M+H)+=450.1.

Workup

  1. customat ambient temperature
  2. concentrationThe solvent was concentrated to 100 mL
  3. extractionthe product was extracted with EtOAc
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-6f3c32b89e8d4dd8aa2d72f9d8fd3c61
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

Loading…