Acetonitrile → {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

HRID 68579

Reaction equation

HRID 68579 reaction equation
[CH3:1][C:2]1[O:3][C:4]([C:9]2[CH2:13][C:12]([C:18]3[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[C:20]([Cl:26])[CH:19]=3)([C:14]([F:17])([F:16])[F:15])[O:11][N:10]=2)=[CH:5][C:6]=1[CH:7]=O.[C:27](NC(=O)[O-])([CH3:30])([CH3:29])[CH3:28].FC(F)(F)[C:37]([OH:39])=[O:38].C([SiH](CC)CC)C.C(#[N:51])C>C(OCC)(=O)C>[C:27]([O:39][C:37](=[O:38])[NH:51][CH2:7][C:6]1[CH:5]=[C:4]([C:9]2[CH2:13][C:12]([C:18]3[CH:23]=[C:22]([Cl:24])[C:21]([Cl:25])=[C:20]([Cl:26])[CH:19]=3)([C:14]([F:15])([F:16])[F:17])[O:11][N:10]=2)[O:3][C:2]=1[CH3:1])([CH3:30])([CH3:29])[CH3:28]

Participants

7

Reactant 5

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 21252905Tert-butylcarbamateHCID 867066532-Methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-carbaldehyde

Product 1

HCID 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

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-methyl-5-[5-(3,4,5-trichloro-phenyl)-5-trifluoromethyl-4,5-dihydro-isoxazol-3-yl]-furan-3-carbaldehyde (2.15 g), tert-butylcarbamate (1.80 g), trifluoroacetic acid (0.78 ml) and triethylsilane (2.48 ml) in acetonitrile (23 ml) is stirred at room temperature for 20 hours. After diluting with ethyl acetate, the reaction mixture is quenched with a saturated solution of NaHCO3. The organic phase is separated and the aqueous phase is extracted once with ethyl acetate. The combined organic phases are washed with a saturated solution of NaHCO3 and with a saturated aqueous solution of NaCl, dried over MgSO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield {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 (2.10 g, compound 2.4 in Table 2) as a light yellow foam. MS (HPLC/MS): 527 (MH+).

Workup

  1. customthe reaction mixture is quenched with a saturated solution of NaHCO3
  2. customThe organic phase is separated
  3. extractionthe aqueous phase is extracted once with ethyl acetate
  4. washThe combined organic phases are washed with a saturated solution of NaHCO3 and with a saturated aqueous solution of NaCl
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customThe crude product is purified on a semi-preparative HPLC

Sources & evidence

ORD record
ord-0c542b814e364c0b824ea24492074314
Source dataset
uspto-grants-2014_09
Patent number
US08822466B2

Linked notes

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