Trifluoroacetic acid → C-{2-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-yl}-methylamine

HRID 68580

Reaction equation

HRID 68580 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][CH2:15][C:16]1[CH:20]=[C:19]([C:21]2[CH2:25][C:24]([C:30]3[CH:35]=[C:34]([Cl:36])[C:33]([Cl:37])=[C:32]([Cl:38])[CH:31]=3)([C:26]([F:29])([F:28])[F:27])[O:23][N:22]=2)[O:18][C:17]=1[CH3:39])(C)(C)C.[OH-].[Na+]>ClCCl>[CH3:39][C:17]1[O:18][C:19]([C:21]2[CH2:25][C:24]([C:30]3[CH:35]=[C:34]([Cl:36])[C:33]([Cl:37])=[C:32]([Cl:38])[CH:31]=3)([C:26]([F:28])([F:27])[F:29])[O:23][N:22]=2)=[CH:20][C:16]=1[CH2:15][NH2:14]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 14798Sodium HydroxideHCID 86706654{2-Methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-ylmethyl}-carbamic acid tert-butyl ester

Product 1

HCID 86706655C-{2-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-yl}-methylamineYield 98.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (6.0 ml) is added to a solution of {2-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-ylmethyl}-carbamic acid tert-butyl ester (2.05 g) in dichloromethane (20 ml). After 45 min at room temperature, an aqueous solution of NaOH (2M) is added until pH 12 is reached and the reaction mixture is extracted three times with dichloromethane. The combined organic phases are washed with a saturated solution of NaCl, dried over Na2SO4 and concentrated in vacuo to yield C-{2-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-yl}-methylamine (1.64 g, compound 2.5 in Table 2) as a light yellow foam. The crude product obtained is used without further purification. MS (HPLC/MS): 410 (MH), Retention time: 1.27 min.

Workup

  1. extractionthe reaction mixture is extracted three times with dichloromethane
  2. washThe combined organic phases are washed with a saturated solution of NaCl
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a3d259fbdfa2492fa1f1c34f1efc80a0
Source dataset
uspto-grants-2014_09
Patent number
US08822466B2

Linked notes

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