Methanol → HCID 57937315, compound

HRID 1435498Notes

Reaction equation

HRID 1435498 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[CH2:31][CH2:30][CH2:29][C@@H:28]([C:32]([O:34]CC)=[O:33])[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[CH2:31][CH2:30][CH2:29][C@@H:28]([C:32]([OH:34])=[O:33])[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 57937352HCID 57937352, compound

Product 1

HCID 57937315HCID 57937315, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

NaOH (0.5 mL, 2 M, 1.0 mmol) was added to a solution of ethyl (3R)-1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}piperidine-3-carboxylate (255 mg, 0.52 mmol) in a 1:1 mixture of MeOH:H2O (10 mL) at ambient temperature. The reaction mixture was stirred overnight and diluted with water (50 mL). The solvent was concentrated to 50 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: 236 mg (98%); MS (ESI) (M+H)+=464.1.

Workup

  1. customat ambient temperature
  2. concentrationThe solvent was concentrated to 50 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-6887dc6434ed4e87913d250e5eb8eec6
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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