Heptane → (R)-4-(4-oxo-1-(phenylthio)butan-2-ylamino)-3-(trifluoromethylsulfonyl)benzenesulfonamide
Reaktionsgleichung
[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]=1Komponenten
8
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- -78 °C
Versuchsvorschrift
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).
Aufarbeitung
- 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
Quellen und Nachweise
- ORD-Eintrag
- ord-64bf9085bea54b5580bf6444143b07f2
- Quelldatensatz
- uspto-grants-2015_04
- Patentnummer
- US09018381B2
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