Triethylamine → N(2,2,4,4-tetramethyltetrahydrothiophene-3-yl)-t-butoxycarbonyl-D-serine amide
Reaktionsgleichung
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C:12]([OH:14])=O)[CH2:10][OH:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C(N(CC)CC)C.ClC(OCC)=O.[NH2:28][CH:29]1[C:33]([CH3:35])([CH3:34])[CH2:32][S:31][C:30]1([CH3:37])[CH3:36]>C(OCC)(=O)C.O1CCCC1>[CH3:36][C:30]1([CH3:37])[CH:29]([NH:28][C:12](=[O:14])[C@@H:9]([CH2:10][OH:11])[NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[C:33]([CH3:35])([CH3:34])[CH2:32][S:31]1Komponenten
Edukt 4
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 2
Reaktionsbedingungen
- Temperatur
- -20 °C
Versuchsvorschrift
To a solution of 2.26 g. (11 mmole) of N-t-butoxycarbonyl-D-serine in 75 ml. of tetrahydrofuran is added 1.47 ml. (10 mmole) of triethylamine and the mixture cooled to -10° C. At this temperature is added 0.96 ml. (10 mmole) of ethyl chloroformate and stirring continued for 15 minutes. After cooling to -20° C., 1.6 g. (10 mmole) of dl-3-amino-2,2,4,4-tetramethyltetrahydrothiophene is added and the resulting mixture is allowed to warm to room temperature. Ethyl acetate is added and the mixture is washed twice with 50 ml. portions of 5% (by weight) aqueous citric acid, aqueous sodium bicarbonate (1 ×50 ml.) and saturated brine (1 ×50 ml.). The organic layer is dried (Na2SO4) and evaporated to dryness at reduced pressure to afford N(2,2,4,4-tetramethyltetrahydrothiophene-3-yl)-t-butoxycarbonyl-D-serine amide. This product is used without further purification in the next step. ##STR113##
Aufarbeitung
- additionAt this temperature is added 0.96 ml
- temperatureto warm to room temperature
- washthe mixture is washed twice with 50 ml
- dry with materialThe organic layer is dried (Na2SO4)
- customevaporated to dryness at reduced pressure
Quellen und Nachweise
- ORD-Eintrag
- ord-ad3a72af891148798a79730099d001e1
- Quelldatensatz
- uspto-grants-1983_08
- Patentnummer
- US04399163
Notizen zur Reaktion
Wird geladen…