Hydrochloric Acid → Trans-2-[(3,5-bistrifluoromethyl phenyl)-aminocarbonyl]-cyclobutane carboxylic acid

HRID 543364Notes

Reaction equation

HRID 543364 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([C@H:16]2[CH2:19][CH2:18][C@H:17]2[C:20]([OH:22])=[O:21])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.Cl>[OH-].[Na+]>[F:1][C:2]([F:23])([F:24])[C:3]1[CH:4]=[C:5]([NH:13][C:14]([C@@H:16]2[CH2:19][CH2:18][C@H:17]2[C:20]([OH:22])=[O:21])=[O:15])[CH:6]=[C:7]([C:9]([F:12])([F:10])[F:11])[CH:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 18607497Cis-2-[(3,5-bistrifluoromethyl phenyl)-aminocarbonyl]-cyclobutane carboxylic acid

Product 1

HCID 13376256Trans-2-[(3,5-bistrifluoromethyl phenyl)-aminocarbonyl]-cyclobutane carboxylic acidYield 68%

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

5.0 g of cis-2-[(3,5-bistrifluoromethyl phenyl)-aminocarbonyl]-cyclobutane carboxylic acid was reacted at a temperature of 50° C. for three hours in 10% aqueous caustic soda solution. The products were neutralized with dilute hydrochloric acid, extracted with ethyl acetate and then recrystallized from acetonitrile to give 3.4 g of the title compounds (yield: 68%).

Workup

  1. extractionextracted with ethyl acetate
  2. customrecrystallized from acetonitrile

Sources & evidence

ORD record
ord-a3c3610774a2403691a5e8fbac39d2fc
Source dataset
uspto-grants-1987_04
Patent number
US04661630

Reaction notes

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