1,8-Diazabicyclo(5.4.0)undec-7-ene → 6-allyl-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one

HRID 403574

반응식

HRID 403574 반응식
Cl[CH2:2][CH2:3][C:4]([C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1)([OH:8])[CH2:5][CH:6]=[CH2:7].[N:16]([C@@H:19]([CH3:24])[C:20]([CH3:23])([CH3:22])[CH3:21])=[C:17]=[O:18].C1CCN2C(=NCCC2)CC1>C1COCC1.CCOC(C)=O>[CH2:5]([C:4]1([C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[O:8][C:17](=[O:18])[N:16]([C@H:19]([C:20]([CH3:23])([CH3:22])[CH3:21])[CH3:24])[CH2:2][CH2:3]1)[CH:6]=[CH2:7]

참가 물질

6

반응물 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 12169316(S)-3-isocyanato-2,2-dimethyl-butaneHCID 534729381-Chloro-3-(4-fluorophenyl)hex-5-en-3-ol

생성물 1

HCID 584852576-allyl-3-((S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one수율 11.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

A mixture of 1-chloro-3-(4-fluorophenyl)hex-5-en-3-ol (500 mg, 2.19 mmol), (S)-3-isocyanato-2,2-dimethyl-butane (845 mg, 5.58 mmol), and DBU (681 mg, 5.9 mmol) in THF (10 mL) was heated to reflux for 25 h. The mixture was diluted with EtOAc and washed with 1 N aq HCl. The aqueous phase was extracted with EtOAc (3×). The combined organic phase was dried over Na2SO4. After the solvents were evaporated, the crude product was purified by column to give 6-allyl-3-((2S)-3,3-dimethylbutan-2-yl)-6-(4-fluorophenyl)-1,3-oxazinan-2-one (80 mg, crude).

후처리

  1. temperaturewas heated
  2. temperatureto reflux for 25 h
  3. washwashed with 1 N aq HCl
  4. extractionThe aqueous phase was extracted with EtOAc (3×)
  5. dry with materialThe combined organic phase was dried over Na2SO4
  6. customAfter the solvents were evaporated
  7. customthe crude product was purified by column

출처 및 근거

ORD 기록
ord-6e39b42537b94cbf88c34937e4d880c9
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08748444B2

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