Methyl iodide → (5-Cyclopropyl-4-methyl-isoxazol-3-yl)-carbamic acid phenyl ester

HRID 45158

반응식

HRID 45158 반응식
[C:1]1([O:7][C:8](=[O:18])[NH:9][C:10]2[CH:14]=[C:13]([CH:15]3[CH2:17][CH2:16]3)[O:12][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Li+].[CH3:20]CC[CH2-].C(=O)=O.CC(C)=O.CI>C1COCC1>[C:1]1([O:7][C:8](=[O:18])[NH:9][C:10]2[C:14]([CH3:20])=[C:13]([CH:15]3[CH2:17][CH2:16]3)[O:12][N:11]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

참가 물질

6

반응물 4

HCID 6328Methyl iodideHCID 61028n-Butyl lithiumHCID 18522661Acetone cardiceHCID 59394551(5-Cyclopropyl-isoxazol-3-yl)-carbamic acid phenyl ester

생성물 1

HCID 59394495(5-Cyclopropyl-4-methyl-isoxazol-3-yl)-carbamic acid phenyl ester

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

(5-Cyclopropyl-isoxazol-3-yl)-carbamic acid phenyl ester (0.368 g, 1.51 mmol) is dissolved in THF (10 mL) and cooled to −78° C. and flushed with nitrogen. N-butyllithium (2.17 mL, 3.47 mmol) is then added. The mixture is stirred in the dry ice/acetone bath for 30 minutes. Methyl iodide (0.10 mL, 1.66 mmol) is added neat and the reaction is stirred for 2 hours at −78° C. The reaction is quenched (0° C.) with 20 mL of a saturated solution of ammonium chloride, diluted with ethyl acetate and the organic layer is removed, dried (sodium sulfate) and concentrated to an oil that is purified via FCC (0-40% ethyl acetate:heptanes) to give the title compound as an oil. MS (ESI) m/z 259.20 (M+1).

후처리

  1. customflushed with nitrogen
  2. customThe reaction is quenched (0° C.) with 20 mL of a saturated solution of ammonium chloride
  3. additiondiluted with ethyl acetate
  4. customthe organic layer is removed
  5. dry with materialdried (sodium sulfate)
  6. concentrationconcentrated to an oil that
  7. customis purified via FCC (0-40% ethyl acetate:heptanes)

출처 및 근거

ORD 기록
ord-7f3f3842e56e4a07967d61e5674b95f7
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08541432B2

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