Hydrochloric Acid → 4-(2-Tert-butoxycarbonylaminomethylcyclopropyl)-2,3,5-trifluorobenzoic acid

HRID 981273Notes

Reaction equation

HRID 981273 reaction equation
[C:1]([O:5][C:6]([N:8]([CH2:13][CH:14]1[CH2:16][CH:15]1[C:17]1[C:27]([F:28])=[CH:26][C:20]([C:21]([O:23]CC)=[O:22])=[C:19]([F:29])[C:18]=1[F:30])C(OC)=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[OH-].[Na+].O.Cl>C(O)C.C(OCC)(=O)C>[C:1]([O:5][C:6]([NH:8][CH2:13][CH:14]1[CH2:16][CH:15]1[C:17]1[C:27]([F:28])=[CH:26][C:20]([C:21]([OH:23])=[O:22])=[C:19]([F:29])[C:18]=1[F:30])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 15136265ethyl 4-[2-(N-tert-butoxycarbonyl-N-methoxycarbonylaminomethyl)cyclopropyl]-2,3,5-trifluorobenzoate

Product 1

HCID 151362664-(2-Tert-butoxycarbonylaminomethylcyclopropyl)-2,3,5-trifluorobenzoic acidYield 98.1%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

In 60 ml of ethanol was dissolved 5.22 g of ethyl 4-[2-(N-tert-butoxycarbonyl-N-methoxycarbonylaminomethyl)cyclopropyl]-2,3,5-trifluorobenzoate. To the resulting solution was added 60 ml of a 1N aqueous sodium hydroxide solution. The resulting mixture was stirred at room temperature for 2 hours. To the reaction mixture was added 60 ml of water and the resulting mixture was adjusted to pH 8 with 6N hydrochloric acid. Then, 150 ml of ethyl acetate was added thereto. The aqueous layer was separated and 100 ml of ethyl acetate was added thereto. The resulting mixture was adjusted to pH 2 with 6N hydrochloric acid. The organic layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure to obtain 4.10 g (98.1%) of 4-(2-tert-butoxycarbonylaminomethylcyclopropyl)-2,3,5-trifluorobenzoic acid.

Workup

  1. customThe aqueous layer was separated
  2. addition100 ml of ethyl acetate was added
  3. customThe organic layer was separated
  4. washwashed with water
  5. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  6. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-c61ad46d948040cfadcd7653bd7a1cf0
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

Loading…