Sodium Hydroxide → (E)-2-[3-chloro-4-(5-methyl-tetrazol-1-yl)-phenyl]-3-cyclohexyl-acrylic acid

HRID 1936403Notes

Reaction equation

HRID 1936403 reaction equation
C[O:2][C:3](=[O:25])/[C: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)=[CH: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](/[C:4](=[CH: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 69692650(E)-2-[3-chloro-4-(5-methyl-tetrazol-1-yl)-phenyl]-3-cyclohexyl-acrylic acid methyl ester

Product 1

HCID 69691556(E)-2-[3-chloro-4-(5-methyl-tetrazol-1-yl)-phenyl]-3-cyclohexyl-acrylic acidYield 100.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
47.5 °C

Procedure

A solution of (E)-2-[3-chloro-4-(5-methyl-tetrazol-1-yl)-phenyl]-3-cyclohexyl-acrylic acid methyl ester (209 mg, 0.58 mmol) in ethanol (3 mL) was treated with a 1N aqueous sodium hydroxide solution (1.2 mL). The solution was heated at 45-50° C. for 15 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 (10 mL) and extracted with diethyl ether (1×30 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 (2×20 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 (E)-2-[3-chloro-4-(5-methyl-tetrazol-1-yl)-phenyl]-3-cyclohexyl-acrylic acid (203 mg, 99%) as a brown solid: FAB-HRMS m/e calcd for C17H19ClN4O2 (M+H)+ 347.1275, found 347.1283.

Workup

  1. concentrationThe reaction mixture was then concentrated in vacuo
  2. customto remove ethanol
  3. additionthe residue was diluted with water (10 mL)
  4. extractionextracted with diethyl ether (1×30 mL)
  5. customto remove any neutral impurities
  6. extractionThe resulting acid was extracted into ethyl acetate (2×20 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-f4fa40c150e24990894d229f79309381
Source dataset
uspto-grants-2002_05
Patent number
US06388088B1

Reaction notes

Loading…