Hydrochloric Acid → 4-(1-Benzyloxycarbonylaminocyclopropyl)-2,3,5,6tetrafluorobenzoic acid

HRID 981274Notes

Reaction equation

HRID 981274 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:15]2[C:24]([F:25])=[C:23]([F:26])[C:18]([C:19]([O:21]C)=[O:20])=[C:17]([F:27])[C:16]=2[F:28])[CH2:14][CH2:13]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].O.Cl>CO.O1CCOCC1.C(OCC)(=O)C>[CH2:1]([O:8][C:9]([NH:11][C:12]1([C:15]2[C:16]([F:28])=[C:17]([F:27])[C:18]([C:19]([OH:21])=[O:20])=[C:23]([F:26])[C:24]=2[F:25])[CH2:13][CH2:14]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 15136259Methyl 4-(1-benzyloxycarbonylaminocyclopropyl)-2,3,5,6-tetrafluorobenzoate

Product 1

HCID 100454814-(1-Benzyloxycarbonylaminocyclopropyl)-2,3,5,6tetrafluorobenzoic acidYield 97.9%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

In a mixture of 14 ml of methanol and 14 ml of dioxane was dissolved 1.8 g of methyl 4-(1-benzyloxycarbonylaminocyclopropyl)-2,3,5,6-tetrafluorobenzoate. To the resulting solution was added 14 ml of a 1N aqueous sodium hydroxide solution. The resulting mixture was stirred at room temperature for 1 hour. To the reaction mixture was added 50 ml of water. The resulting mixture was adjusted to pH 1 with 2N hydrochloric acid, and 50 ml of ethyl acetate was added thereto. 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, and n-hexane was added to the residue obtained. The resulting crystals were collected by filtration to obtain 1.7 g (yield: 97.7%) of 4-(1-benzyloxycarbonylaminocyclopropyl)-2,3,5,6tetrafluorobenzoic acid.

Workup

  1. additionwas added
  2. customThe organic layer was separated
  3. washwashed with water
  4. dry with materiala saturated aqueous sodium chloride solution in this order, and dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by distillation under reduced pressure, and n-hexane
  6. additionwas added to the residue
  7. customobtained
  8. filtrationThe resulting crystals were collected by filtration

Sources & evidence

ORD record
ord-8742601296844af4835a876469d549af
Source dataset
uspto-grants-1991_02
Patent number
US04990508

Reaction notes

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