Heptane → (R)-4-(4-oxo-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)benzenesulfonamide
반응식
[C:1]1([S:7][CH2:8][C@H:9]([NH:15][C:16]2[CH:21]=[CH:20][C:19]([S:22](=[O:25])(=[O:24])[NH2:23])=[CH:18][C:17]=2[S:26]([C:29]([F:32])([F:31])[F:30])(=[O:28])=[O:27])[CH2:10][C:11](OC)=[O:12])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CC(C[AlH]CC(C)C)C.CCCCCCC.[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C(Cl)Cl.O.CO>[O:12]=[CH:11][CH2:10][C@@H:9]([NH:15][C:16]1[CH:21]=[CH:20][C:19]([S:22]([NH2:23])(=[O:24])=[O:25])=[CH:18][C:17]=1[S:26]([C:29]([F:30])([F:31])[F:32])(=[O:28])=[O:27])[CH2:8][S:7][C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1참가 물질
8
반응물 4
생성물 1
시약·촉매·용매 3
반응 조건
- 온도
- -78 °C
실험 절차
A mixture of (R)-methyl 4-(phenylthio)-3-(4-sulfamoyl-2-(trifluoromethylsulfonyl)phenylamino)butanoate (INTERMEDIATE 7, 3.1 g, 6.05 mmol) in DCM (155 ml) was cooled to −78° C. and DIBAL-H in heptane (18.1 ml, 18.1 mmol) was added dropwise. After addition was complete, the mixture was stirred for 3 hours at −78° C. Methanol (8 ml) and an aqueous solution of Rochelle's salt (15.0 ml) were added sequentially, and the reaction mixture was warmed to r.t. Water (150 ml) was added to the reaction, and the layers were separated. The organic layer was washed with water, dried (Na2SO4), and concentrated in vacuo to afford the title compound (2.9 g, yield: almost quantitative).
후처리
- additionAfter addition
- temperaturethe reaction mixture was warmed to r.t
- customthe layers were separated
- washThe organic layer was washed with water
- dry with materialdried (Na2SO4)
- concentrationconcentrated in vacuo
출처 및 근거
- ORD 기록
- ord-ed448480db744c28ad201ba76fbbe449
- 출처 데이터셋
- uspto-grants-2016_02
- 특허 번호
- US09248140B2
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