Ethyl Acetate → HCID 178445698, compound

HRID 967639Notes

Reaction equation

HRID 967639 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-c1a2d623d5e64487991f115162646dca
Source dataset
uspto-grants-2005_10
Patent number
US06953812B2

Reaction notes

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