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

HRID 492838Notes

Reaction equation

HRID 492838 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[C:9]([O:11][C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[O:20])=[CH:14][C:13]=2[F:29])[CH:8]=[CH:7][N:6]=1)=[O:4].[OH-].[Li+].Cl>CO.CN(C)C=O.O>[CH2:22]([O:21][C:19]([NH:18][C:15]1[CH:16]=[CH:17][C:12]([O:11][C:9]2[CH:8]=[CH:7][N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=2)=[C:13]([F:29])[CH:14]=1)=[O:20])[C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 576777514-(4-Benzyloxycarbonylamino-2-fluorophenoxy)pyridine-2-carboxylic acid methyl ester

Product 1

HCID 231529624-(4-Benzyloxycarbonylamino-2-fluorophenoxy)pyridine-2-carboxylic acidYield 92.3%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

After dissolving 4-(4-benzyloxycarbonylamino-2-fluorophenoxy)pyridine-2-carboxylic acid methyl ester (10.7 g) in methanol (450 ml) and N,N-dimethylformamide (150 ml), water (75 ml) and lithium hydroxide (1.36 g) were added and the mixture was stirred for 1 hour at room temperature. After adding 1N hydrochloric acid (100 ml), the reaction mixture was concentrated under reduced pressure, ethyl acetate (500 ml) was added for partition, and the precipitated solid was filtered. The resultant solid was washed with water and hexane and then subjected to aeration drying. The organic layer of the obtained filtrate was washed with water (100 ml×2) and brine (200 ml) and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and then the obtained solid was washed with water and hexane and subjected to aeration drying. This solid was combined with the previously obtained solid and dried at 60° C. overnight to provide the title compound (9.53 g, 92.3%) as white powder.

Workup

  1. additionwere added
  2. concentrationthe reaction mixture was concentrated under reduced pressure, ethyl acetate (500 ml)
  3. additionwas added
  4. customfor partition
  5. filtrationthe precipitated solid was filtered
  6. washThe resultant solid was washed with water and hexane
  7. customdrying
  8. washThe organic layer of the obtained filtrate was washed with water (100 ml×2) and brine (200 ml)
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationThe solvent was distilled off under reduced pressure
  11. washthe obtained solid was washed with water and hexane
  12. customdrying
  13. customdried at 60° C. overnight

Sources & evidence

ORD record
ord-530c2c8e95f7405da2465f02008f1177
Source dataset
uspto-grants-2009_05
Patent number
US07531532B2

Reaction notes

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