Chloroform → HCID 22713757, compound

HRID 352163Notes

Reaction equation

HRID 352163 reaction equation
[N+:1]([CH:4]1[CH2:9][CH2:8][CH2:7][CH:6]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH2:5]1)([O-])=O.[CH2:15](N(CC)CC)C.[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=1[C:30]1[C:34]([C:35](Cl)=[O:36])=[C:33]([CH3:38])[O:32]N=1.C(Cl)(Cl)Cl>C(O)(=O)C.ClCCl.O=[Pt]=O>[Cl:22][C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([F:29])[C:24]=1[C:30]1[C:34]([C:35]([NH:1][CH:4]2[CH2:9][CH2:8][CH2:7][CH:6]([CH2:10][C:11]([O:13][CH3:14])=[O:12])[CH2:5]2)=[O:36])=[C:33]([CH3:38])[O:32][CH:15]=1

Participants

8

Reactant 4

HCID 6212ChloroformHCID 8471TriethylamineHCID 27365813-(2-Chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chlorideHCID 22713860HCID 22713860, compound

Product 1

HCID 22713757HCID 22713757, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 345198Adams' catalystCatalystHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-(3-nitrocyclohexyl)acetate (13.8 g, 71.0 mmol) in 200 mL of acetic acid was added 6.9 g of PtO2. The mixture was hydrogenated overnight at ambient temperature and 60 psi, then was filtered through celite and concentrated to dryness. To a solution of the residue, 8.8 g (38.0 mmol) in 200 mL of dichloromethane was added 27 mL (190 mmol) of triethylamine and 10.4 g (38.0 mmol) of 3-(2-chloro-6-fluorophenyl)-5-methylisoxazole-4-carbonyl chloride. The mixture was stirred overnight at ambient temperature then chloroform was added. The organics were washed with 0.5N HCl, saturated sodium bicarbonate, brine, dried over sodium sulfate, filtered and concentrated to dryness. The resulting residue was chromatographed on silica gel using 5% acetone/dichloromethane to yield 4.43 g (29%) of the desired mixture of isomers as a colorless, viscous oil. 1H—NMR is consistent with structure. MS (ion spray) 409.2 (M+1).

Workup

  1. filtration60 psi, then was filtered through celite and
  2. concentrationconcentrated to dryness
  3. washThe organics were washed with 0.5N HCl, saturated sodium bicarbonate, brine
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated to dryness
  7. customThe resulting residue was chromatographed on silica gel using 5% acetone/dichloromethane

Sources & evidence

ORD record
ord-0399f687d1554fd8becfd93196c47b9f
Source dataset
uspto-grants-2004_06
Patent number
US06743794B2

Reaction notes

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