HCID 73509154, compound → HCID 19023603, compound

HRID 1590250Notes

Reaction equation

HRID 1590250 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12](=[O:13])[C:11](=[N:14]O)[CH:10]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:9]1>CCO>[NH2:14][CH:11]1[C:12](=[O:13])[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[F:1])[CH2:9][CH:10]1[C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17]

Participants

3

Reactant 1

HCID 73509154HCID 73509154, compound

Product 1

HCID 19023603HCID 19023603, compoundYield 72.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of oxime of Example O (1.23 g, 3.99 mmol) in EtOH was hydrogenated at 1000 psi on Pd/C at 70° C. for 24 h. The solvent was removed in vacuo to give an oil which was chromatographed on silica gel eluting with 2% EtOH/CH2Cl2 to give the title compound (850 mg, 72%) as a solid. Anal calcd for C15H19N2O3F: C, 61.21; H, 6.51; N, 9.52; F, 6.45. Found: C, 60.87; H, 6.61; N, 9.32; F, 6.10. MS calcd for C15H19N2O3F 294, found 294. DSC=71.2°-74.9° C. at 76.6 J/g.

Workup

  1. customThe solvent was removed in vacuo
  2. customto give an oil which
  3. customwas chromatographed on silica gel eluting with 2% EtOH/CH2Cl2

Sources & evidence

ORD record
ord-e1fe25dc6cd849f0beb44f594594b273
Source dataset
uspto-grants-1993_04
Patent number
US05202344

Reaction notes

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