Sodium Hydroxide → 3-Cyclopentyl-2-[4-methanesulfonyl-3-(5-methyl-tetrazol-1-yl)-phenyl]-propionic acid

HRID 841233Notes

Reaction equation

HRID 841233 reaction equation
C[O:2][C:3](=[O:27])[CH:4]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[C:13]([N:21]2[C:25]([CH3:26])=[N:24][N:23]=[N:22]2)[CH:12]=1)[CH2:5][CH:6]1[CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+]>C(O)C>[CH:6]1([CH2:5][CH:4]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:18])=[O:19])=[C:13]([N:21]3[C:25]([CH3:26])=[N:24][N:23]=[N:22]3)[CH:12]=2)[C:3]([OH:27])=[O:2])[CH2:10][CH2:9][CH2:8][CH2:7]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 696913393-Cyclopentyl-2-[4-methanesulfonyl-3-(5-methyl-tetrazol-1-yl)-phenyl]propionic acid methyl ester

Product 1

HCID 184343533-Cyclopentyl-2-[4-methanesulfonyl-3-(5-methyl-tetrazol-1-yl)-phenyl]-propionic acidYield 89.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
47.5 °C

Procedure

A solution of 3-cyclopentyl-2-[4-methanesulfonyl-3-(5-methyl-tetrazol-1-yl)-phenyl]-propionic acid methyl ester (102 mg, 0.26 numol) in ethanol (3 mL) was treated with a 1N aqueous sodium hydroxide solution (0.6 mL). The solution was heated at 45-50° C. for 5 h, at which time, thin layer chromatography analysis of the reaction mixture indicated the absence of starting material. The reaction mixture was concentrated in vacuo to remove ethanol. The residue was diluted with water (20 mL) and extracted with diethyl ether (1×30 mL) to remove any neutral impurities. The aqueous layer was then acidified with a 1N aqueous hydrochloric acid solution, and the resulting acid was extracted into ethyl acetate (2×25 mL). The combined organic layers were washed with a saturated aqueous sodium chloride solution (1×50 mL), dried over anhydrous magnesium sulfate, filtered, and concentrated in vacuo to afford 3-cyclopentyl-2-[4-methanesulfonyl-3-(5-methyl-tetrazol-1-yl)-phenyl]-propionic acid (88 mg, 89%) as an amorphous white solid: EI-HRMS m/e calcd for C17H22N4O4S (M+) 378.1362, found 378.1364.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto remove ethanol
  3. additionThe residue was diluted with water (20 mL)
  4. extractionextracted with diethyl ether (1×30 mL)
  5. customto remove any neutral impurities
  6. extractionthe resulting acid was extracted into ethyl acetate (2×25 mL)
  7. washThe combined organic layers were washed with a saturated aqueous sodium chloride solution (1×50 mL)
  8. dry with materialdried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-70f12f77b0b740a9b785bbf7dc85b934
Source dataset
uspto-grants-2002_04
Patent number
US06369232B1

Reaction notes

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