Hydrochloric Acid → HCID 59253266, compound

HRID 386869Notes

Reaction equation

HRID 386869 reaction equation
[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([C:17]([CH3:23])([CH3:22])[C:18]([O:20]C)=[O:19])(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:3][CH2:2]1.[OH-].[Na+].Cl>CO.C1COCC1>[CH:1]1([CH2:4][N:5]2[C:9]3[CH:10]=[CH:11][C:12]([S:14]([C:17]([CH3:22])([CH3:23])[C:18]([OH:20])=[O:19])(=[O:16])=[O:15])=[CH:13][C:8]=3[N:7]=[C:6]2[CH2:24][C:25]([CH3:28])([CH3:27])[CH3:26])[CH2:2][CH2:3]1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 59253268HCID 59253268, compound

Product 1

HCID 59253266HCID 59253266, compoundYield 82.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 2-{[1-(cyclopropylmethyl)-2-(2,2-dimethyl-propyl)-1H-benzoimidazol-5-yl]sulfonyl}-2-methylpropanoate (1.65 g, 4.06 mmol) in methanol (7.5 mL) and THF (7.5 mL) is added 2N aqueous NaOH solution at room temperature. The reaction is stirred for 3 h, then acidified with 2N aqueous HCl solution to pH 4 and concentrated under reduced pressure. The residue is partitioned between water (75 mL) and DCM (75 mL). The acidic aqueous layer is extracted with DCM (50 mL×2) and the combined organic extracts are dried over Na2SO4, filtered and the filtrated is concentrated under reduced pressure to afford 1.31 g of 2-{[1-(cyclopropylmethyl)-2-(2,2-dimethyl-propyl)-1H-benzoimidazol-5-yl]sulfonyl}-2-methylpropanoic acid. Yield: 82%, ES-MS: 393 [M+H]

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue is partitioned between water (75 mL) and DCM (75 mL)
  3. extractionThe acidic aqueous layer is extracted with DCM (50 mL×2)
  4. dry with materialthe combined organic extracts are dried over Na2SO4
  5. filtrationfiltered
  6. concentrationthe filtrated is concentrated under reduced pressure

Sources & evidence

ORD record
ord-50920f765b4b4c178057c2ac7435d430
Source dataset
uspto-grants-2013_02
Patent number
US08372874B2

Reaction notes

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