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

HRID 1435450Notes

Reaction equation

HRID 1435450 reaction equation
[OH-].[Li+].[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[CH:30]=[CH:29][C:28]([C:31]([O:33]C)=[O:32])=[CH:27]3)(=[O:25])=[O:24])=[CH:22][C:9]=2[N:8]=1)([CH3:6])([CH3:5])[CH3:4]>C1COCC1.O>[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[CH:30]=[CH:29][C:28]([C:31]([OH:33])=[O:32])=[CH:27]3)(=[O:25])=[O:24])=[CH:22][C:9]=2[N:8]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

4

Reactant 2

HCID 3939Lithium HydroxideHCID 23660111methyl 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carboxylate

Product 1

HCID 579373191-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carboxylic acid

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

Lithium hydroxide (25 mg, 1.0 mmol) was added to mixture of methyl 1-{[2-tert-butyl-1-(tetrahydro-2H-pyran-4-ylmethyl)-1H-benzimidazol-5-yl]sulfonyl}-1H-pyrrole-3-carboxylate (90 mg, 0.2 mmol) in 10 mL of THF-H2O (7:3) at 0° C. The reaction mixture was stirred overnight at room temperature and acidified to pH=1. Upon evaporation and dried in vacuo, the residue was dissolved in DMF (10 mL) and then used directly for step A. Purity:>80% (checked by LCMS). MS (ESI) (M+H)+=445.99.

Workup

  1. customUpon evaporation
  2. customdried in vacuo
  3. dissolutionthe residue was dissolved in DMF (10 mL)

Sources & evidence

ORD record
ord-cceb73458c21441e9cba4e8d4368e9c6
Source dataset
uspto-grants-2009_11
Patent number
US07615642B2

Reaction notes

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