Hydrochloric Acid → 4-(4-Benzyloxycarbonylamino-3-fluorophenoxy)pyridine-2-carboxylic acid

HRID 492841Notes

Reaction equation

HRID 492841 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:29]=[CH:28][C:15]([O:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([C:23]([O:25]CC)=[O:24])[CH:18]=2)=[CH:14][C:13]=1[F:30])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Li+].Cl>C(O)C.O>[CH2:1]([O:8][C:9]([NH:11][C:12]1[CH:29]=[CH:28][C:15]([O:16][C:17]2[CH:22]=[CH:21][N:20]=[C:19]([C:23]([OH:25])=[O:24])[CH:18]=2)=[CH:14][C:13]=1[F:30])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 23153118Ethyl 4-(4-benzyloxycarbonylamino-3-fluorophenoxy)pyridine-2-carboxylate

Product 1

HCID 231530984-(4-Benzyloxycarbonylamino-3-fluorophenoxy)pyridine-2-carboxylic acidYield 72%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

After suspending ethyl 4-(4-benzyloxycarbonylamino-3-fluorophenoxy)pyridine-2-carboxylate (7.51 g) in ethanol (100 ml) and water (20 ml), lithium hydroxide (657 mg) was added at room temperature. The reaction mixture was stirred for 1 hour at room temperature. The reaction mixture was stirred while cooling in an ice bath and then 1N hydrochloric acid (60 ml) was added thereto. After stirring for 5 minutes, the reaction mixture was concentrated. After concentration, the crystals precipitated in the reaction mixture were filtrated, and the crystals were washed with water. The crystals were then dissolved in ethyl acetate-tetrahydrofuran, the solution was dried over anhydrous sodium sulfate. The dried solution was concentrated under reduced pressure. The obtained precipitate was suspended in hexane and the precipitate was filtered. The solid was dried to provide the title compound (5.04 g, 72.0%) as a pale yellow solid.

Workup

  1. additionwas added at room temperature
  2. stirringThe reaction mixture was stirred
  3. temperaturewhile cooling in an ice bath
  4. stirringAfter stirring for 5 minutes
  5. concentrationthe reaction mixture was concentrated
  6. concentrationAfter concentration
  7. customthe crystals precipitated in the reaction mixture
  8. filtrationwere filtrated
  9. washthe crystals were washed with water
  10. dissolutionThe crystals were then dissolved in ethyl acetate-tetrahydrofuran
  11. dry with materialthe solution was dried over anhydrous sodium sulfate
  12. concentrationThe dried solution was concentrated under reduced pressure
  13. filtrationthe precipitate was filtered
  14. customThe solid was dried

Sources & evidence

ORD record
ord-6d5644878580458b9ae93d933cb01b80
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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