Methanol → HCID 57937379, compound

HRID 1435496Notes

Reaction equation

HRID 1435496 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 57937346HCID 57937346, compound

Product 1

HCID 57937379HCID 57937379, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

NaOH (0.15 mL, 2M, 0.3 mmol) was added to a solution of ethyl (3S)-1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}piperidine-3-carboxylate (265 mg, 0.54 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: 220 mg (88%); 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-4048ba9865ae41adb17666887bf290c6
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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