Ammonium Chloride → HCID 68958100, 화합물

HRID 2378055노트

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HRID 2378055 반응식
[C:1]([Si:5]([CH3:24])([CH3:23])[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13](=[N:21][OH:22])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.C[O:31][C:32]([CH:34]1[CH2:36][CH2:35]1)=O.[Cl-].[NH4+]>O1CCCC1.C(OCC)(=O)C>[C:1]([Si:5]([CH3:24])([CH3:23])[O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]([C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:32]([CH:34]3[CH2:36][CH2:35]3)([OH:31])[O:22][N:21]=2)=[CH:9][CH:8]=1)([CH3:2])([CH3:4])[CH3:3]

참가 물질

7

반응물 4

HCID 25517Ammonium ChlorideHCID 76122Methyl cyclopropanecarboxylateHCID 72579577HCID 72579577, 화합물HCID 178418339Butyllithium

생성물 1

HCID 68958100HCID 68958100, 화합물수율 32%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

To a mixture consisting of Example 1, Compound B (3.0 g) in anhydrous tetrahydrofuran (14 mL) at −5° C. under a nitrogen atmosphere is added a solution consisting of 1.6 M n-butyllithium in hexanes (12 mL.) The mixture is stirred between −5 and 0° C. for 30 minutes. To the stirring mixture at 0° C. is added a mixture consisting of cyclopropanecarboxylic acid methyl ester (1.3 g) in tetrahydrofuran (7 mL) and the resultant mixture is stirred for two hours. The mixture is raised to room temperature and is stirred for 18 hours. The mixture is then treated with saturated aqueous ammonium chloride (50 mL) and diluted with ethyl acetate (300 mL.) The organic layer is separated and is washed sequentially with an additional portion of saturated aqueous ammonium chloride (50 mL) and brine solution (50 mL.) The organic layer is separated and is dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure. The concentrate is purified by flash silica gel column chromatography. Elution with dichloromethane then with a mixture of hexanes-ethyl acetate (4:1 v/v) afforded the synthetic intermediate 3-[4-(tert-butyl-dimethyl-silanyloxy)-phenyl]-5-cyclopropyl-4-phenyl-4,5-dihydro-isoxazol-5-ol (1.15 g.)

후처리

  1. additionis added a solution
  2. additionTo the stirring mixture at 0° C. is added a mixture
  3. stirringis stirred for 18 hours
  4. customis separated
  5. washis washed sequentially with an additional portion of saturated aqueous ammonium chloride (50 mL) and brine solution (50 mL.) The organic layer
  6. customis separated
  7. dry with materialis dried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated under reduced pressure
  10. customThe concentrate is purified by flash silica gel column chromatography
  11. washElution with dichloromethane
  12. additionwith a mixture of hexanes-ethyl acetate (4:1 v/v)

출처 및 근거

ORD 기록
ord-8b59125dd8a64c39b499ca35b8ba55cd
출처 데이터셋
uspto-grants-2008_12
특허 번호
US07470715B2

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