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

反応式

HRID 68579 の反応式
[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]

参加物

7

反応物 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

生成物 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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

実験手順

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+).

後処理

  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

出典と根拠

ORDレコード
ord-0c542b814e364c0b824ea24492074314
出典データセット
uspto-grants-2014_09
特許番号
US08822466B2

関連ノート

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