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

反応式

HRID 403574 の反応式
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]

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-6e39b42537b94cbf88c34937e4d880c9
出典データセット
uspto-grants-2014_06
特許番号
US08748444B2

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