Sodium Hydroxide → HCID 57937355, compound

HRID 1435485Notes

Reaction equation

HRID 1435485 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][CH: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.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][CH: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 2

HCID 14798Sodium HydroxideHCID 57937350HCID 57937350, compound

Product 1

HCID 57937355HCID 57937355, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

NaOH (0.75 mL, 2M, 1.5 mmol) was added to a solution of ethyl 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}piperidine-3-carboxylate (158 mg, 0.36 mmol) in 10 mL of MeOH—H2O (1:1) at ambient temperature. The reaction mixture was stirred overnight and diluted with water (40 mL). The solvent was concentrated to 40 mL. The resulting solution was neutralized with HCl solution and the product was extracted with EtOAc and dried over anhydrous Na2SO4. The solvent was concentrated to provide the title compound as white solid. Yield: 108 mg (72%); MS (ESI) (M+H)+=464.0.

Workup

  1. concentrationThe solvent was concentrated to 40 mL
  2. extractionthe product was extracted with EtOAc
  3. dry with materialdried over anhydrous Na2SO4
  4. concentrationThe solvent was concentrated

Sources & evidence

ORD record
ord-0c20be250cf94888b60c4afdcdbdb5db
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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