Sodium Hydroxide → HCID 12019646, compound

HRID 2306367Notes

Reaction equation

HRID 2306367 reaction equation
C[O:2][C:3](=[O:25])[CH:4]([C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:22]([CH3:23])=[N:21][N:20]=[N:19]2)=[C:14]([Cl:24])[CH:13]=1)[CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]1.[OH-].[Na+]>C(O)C>[Cl:24][C:14]1[CH:13]=[C:12]([CH:4]([CH2:5][CH:6]2[CH2:11][CH2:10][CH2:9][CH2:8][CH2:7]2)[C:3]([OH:25])=[O:2])[CH:17]=[CH:16][C:15]=1[N:18]1[C:22]([CH3:23])=[N:21][N:20]=[N:19]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 69692171HCID 69692171, compound

Product 1

HCID 12019646HCID 12019646, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
47.5 °C

Procedure

A solution of 2-[3-chloro-4-(5-methyl-tetrazol-1-yl)-phenyl]-3-cyclohexyl-propionic acid methyl ester (278 mg, 0.76 mmol) in ethanol (6 mL) was treated with a 1N aqueous sodium hydroxide solution (1.5 mL). The solution was heated at 45-50° C. for 5 h, at which time, thin layer chromatography analysis of the mixture indicated the absence of starting material. The reaction mixture was then concentrated in vacuo to remove ethanol, and the residue was diluted with water (20 mL) and extracted with diethyl ether (1×40 mL) to remove any neutral impurities. The aqueous layer was acidified with a 1N aqueous hydrochloric acid solution. The resulting acid was extracted into ethyl acetate (2×50 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 2-[3-chloro-4-(5-methyl-tetrazol-1-yl)-phenyl]-3-cyclohexyl-propionic acid (226 mg, 85%) as an amorphous solid: EI-HRMS m/e calcd for C17H21ClN4O2 (M+) 348.1353, found 348.1354.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customto remove ethanol
  3. additionthe residue was diluted with water (20 mL)
  4. extractionextracted with diethyl ether (1×40 mL)
  5. customto remove any neutral impurities
  6. extractionThe resulting acid was extracted into ethyl acetate (2×50 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-8e9ab5775b374efca54956e0235697d3
Source dataset
uspto-grants-2002_08
Patent number
US06441180B1

Reaction notes

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