Sodium Hydroxide → HCID 57937388, compound

HRID 1435504Notes

Reaction equation

HRID 1435504 reaction equation
[OH-].[Na+].[C:3]([C:7]1[N:11]([CH2:12][CH:13]2[CH2:18][CH2:17][C:16]([F:20])([F:19])[CH2:15][CH2:14]2)[C:10]2[CH:21]=[CH:22][C:23]([S:25]([N:28]3[CH2:33][CH2:32][CH2:31][C@H:30]([C:34]([O:36]CC)=[O:35])[CH2:29]3)(=[O:27])=[O:26])=[CH:24][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][C:16]([F:19])([F:20])[CH2:17][CH2:18]2)[C:10]2[CH:21]=[CH:22][C:23]([S:25]([N:28]3[CH2:33][CH2:32][CH2:31][C@H:30]([C:34]([OH:36])=[O:35])[CH2:29]3)(=[O:27])=[O:26])=[CH:24][C:9]=2[N:8]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 57937302HCID 57937302, compound

Product 1

HCID 57937388HCID 57937388, compound

Reagents, catalysts & solvents 2

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

Procedure

NaOH (2 mL, 2 M, 4.0 mmol) was added to a solution of ethyl (3S)-1-({2-tert-butyl-1-[(4,4-difluorocyclohexyl)methyl]-1H-benzimidazol-5-yl}sulfonyl)piperidine-3-carboxylate (1.4 g, 2.7 mmol) in 80 mL of MeOH—H2O (1:1) at ambient temperature. The reaction mixture was stirred overnight and diluted with water (80 mL). The solvent was concentrated to 80 mL. The resulting solution was neutralized with 2 N HCl. The product was extracted with EtOAc and dried over anhydrous Na2SO4. The solvent was concentrated to provide the title compound as white solid. Yield: 1.3 g (95%); 1H NMR (400 MHz, CDCl3) δ 1.24-1.27 (m, 1 H), 1527-1.39 (m, 1 H), 1.45-1.59 (m, 2 H), 1.62 (s, 9 H), 1.68 (s, 3 H), 1.70-1.86 (m, 4 H), 1.93-2.06 (m, 1 H), 2.08-2.25 (m, 2 H), 2.33 (t, J=12.11 Hz, 1 H), 2.46 (t, J=10.94 Hz, 1 H), 2.53-2.66 (m, 1 H), 3.69 (d, J=11.72 Hz, 1 H), 3.89 (d, J=9.96 Hz, 1 H), 4.31 (d, J=7.23 Hz, 2 H), 7.48 (d, J=8.79 Hz, 1 H), 7.67 (d, J=8.20 Hz, 1 H), 8.26 (s, 1 H); MS (ESI) (M+H)+=498.1.

Workup

  1. concentrationThe solvent was concentrated to 80 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-38675c19ec8c472ca42a04a6acef3c83
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

Loading…