Ethyl Acetate → HCID 178445698, compound

HRID 412439Notes

Reaction equation

HRID 412439 reaction equation
C[O:2][C:3](=[O:39])[C:4]1[CH:9]=[CH:8][C:7]([CH:10]([NH:25][C:26]([NH:28][C@H:29]2[CH2:34][CH2:33][C@H:32]([C:35]([CH3:38])([CH3:37])[CH3:36])[CH2:31][CH2:30]2)=[O:27])[C:11]2[CH:16]=[C:15]([C:17]([F:20])([F:19])[F:18])[CH:14]=[C:13]([C:21]([F:24])([F:23])[F:22])[CH:12]=2)=[CH:6][CH:5]=1.[OH-].[Na+].C(OCC)(=O)C>C(O)C>[F:18][C:17]([F:19])([F:20])[C:15]1[CH:16]=[C:11]([CH:10]([NH:25][C:26]([NH:28][C@H:29]2[CH2:30][CH2:31][C@H:32]([C:35]([CH3:36])([CH3:37])[CH3:38])[CH2:33][CH2:34]2)=[O:27])[C:7]2[CH:6]=[CH:5][C:4]([C:3]([OH:39])=[O:2])=[CH:9][CH:8]=2)[CH:12]=[C:13]([C:21]([F:22])([F:23])[F:24])[CH:14]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 178497946HCID 178497946, compound

Product 1

HCID 178445698HCID 178445698, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Trans-4-[1-(3,5-bis(trifluoromethyl)phenyl)-3-(4-tert-butylcyclohexyl)ureidomethyl]benzoic acid methyl ester (1.4 g) was suspended in absolute ethanol (20 mL), sodium hydroxide (2N, 11 mL) was added and the reaction mixture was gently refluxed for 2 hours. The ethanol was removed in vacuo, additional water (40 mL) was added, pH was adjusted with hydrochloride (4 N) to acidic reaction and then ethyl acetate (200 mL) was added. The organic phase was isolated, washed with water (4×50 mL), dried with magnesium sulphate, filtered and evaporated in vacuo, affording 1.1 g (85%) trans-4-[1-(3,5-bis(trifluoromethyl)phenyl)-3-(4-tert-butylcyclohexyl)ureidomethyl]benzoic acid as a solid.

Workup

  1. temperaturethe reaction mixture was gently refluxed for 2 hours
  2. customThe ethanol was removed in vacuo, additional water (40 mL)
  3. additionwas added
  4. custompH was adjusted with hydrochloride (4 N) to acidic reaction
  5. customThe organic phase was isolated
  6. washwashed with water (4×50 mL)
  7. dry with materialdried with magnesium sulphate
  8. filtrationfiltered
  9. customevaporated in vacuo

Sources & evidence

ORD record
ord-42463037bece4ea28f5aa4664f0a67c8
Source dataset
uspto-grants-2003_05
Patent number
US06562807B2

Reaction notes

Loading…