Hydrochloric Acid → HCID 72794471, compound

HRID 661722Notes

Reaction equation

HRID 661722 reaction equation
Cl.C(OC(=O)[NH:8][CH2:9][CH2:10][O:11][N:12]=[CH:13][C:14]1[CH:19]=[C:18]([C:20](=[O:26])[NH:21][O:22][CH2:23][CH2:24][OH:25])[C:17]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([I:34])=[CH:30][C:29]=2[F:35])=[C:16]([F:36])[C:15]=1[F:37])(C)(C)C.C(=O)(O)[O-].[Na+]>C(OCC)(=O)C>[NH2:8][CH2:9][CH2:10][O:11][N:12]=[CH:13][C:14]1[C:15]([F:37])=[C:16]([F:36])[C:17]([NH:27][C:28]2[CH:33]=[CH:32][C:31]([I:34])=[CH:30][C:29]=2[F:35])=[C:18]([CH:19]=1)[C:20]([NH:21][O:22][CH2:23][CH2:24][OH:25])=[O:26]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 72964235{2-[2,3-Difluoro-4-(2-fluoro-4-iodo-phenylamino)-5-(2-hydroxy-ethoxycarbamoyl)-benzylideneaminooxy]-ethyl}-carbamic acid tert-butyl ester

Product 1

HCID 72794471HCID 72794471, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent2×

Procedure

1 N HCl solution in ethyl acetate (1 ml) was added to a solution of {2-[2,3-difluoro-4-(2-fluoro-4-iodo-phenylamino)-5-(2-hydroxy-ethoxycarbamoyl)-benzylideneaminooxy]-ethyl}-carbamic acid tert-butyl ester (55 mg, 0.31 mmol) prepared in Process A in ethyl acetate (5 ml). This mixture was then stirred at room temperature for 1.5 hours. After the completion of the reaction, the reaction solution was neutralized with saturated sodium bicarbonate solution (50 ml) and extracted with ethyl acetate (100 ml×3). The extract was washed with saturated brine, and the organic layer was dried over anhydrous sodium sulfate and filtered. The solvent was evaporated off under reduced pressure, and the resulting residue was washed with diethyl ether (10 ml) and then recrystallized from methanol to give 5-[(2-amino-ethoxyimino)-methyl]-3,4-difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-benzamide (17.31 mg, 37% yield) as a pale yellow solid.

Workup

  1. customAfter the completion of the reaction
  2. extractionextracted with ethyl acetate (100 ml×3)
  3. washThe extract was washed with saturated brine
  4. dry with materialthe organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customThe solvent was evaporated off under reduced pressure
  7. washthe resulting residue was washed with diethyl ether (10 ml)
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-380ced045d1647d697fd0b0e97ee4523
Source dataset
uspto-grants-2011_12
Patent number
US08084645B2

Reaction notes

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