4-Methylmorpholine → Tert-butyl N-[(3S)-1-bromo-5-methyl-2-oxohexan-3-YL]carbamate

HRID 1743120Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1743120
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:13][CH:14]([CH3:16])[CH3:15])[C:10]([OH:12])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].[CH3:17]N1CCOCC1.ClCCOC=O.[N+](=C)=[N-].[BrH:33].C(O)(=O)C>O1CCCC1.C(OCC)C.O>[Br:33][CH2:17][C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:13][CH:14]([CH3:16])[CH3:15]

Komponenten

9

Edukt 5

HCID 79724-MethylmorpholineHCID 9550DiazomethaneHCID 83170L-Leucine, N-((1,1-dimethylethoxy)carbonyl)-HCID 2467482-Chloroethyl formateHCID 21893785Acetic Acid Mixture with Hydrobromic Acid

Produkt 1

HCID 11034179Tert-butyl N-[(3S)-1-bromo-5-methyl-2-oxohexan-3-YL]carbamate

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 962WaterLösungsmittelHCID 3283Diethyl EtherLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Under atmosphere of argon, to a solution of (2S)-2-(t-butoxycarbonylamino)-4-methylpentanoic acid (t-butoxycarbonyl-L-leucine) (37.4 g) in tetrahydrofuran (800 ml) was added N-methylmorpholine (33 ml) at −25° C. and the mixture was stirred for 10 minutes. To the mixture was added chloroethylformate (15.8 ml) and the mixture was stirred for 20 minutes. Thereto was added a solution of diazomethane in diethyl ether and the mixture was stirred for another 2 hours. Thereto was added a mixture of 47% hydrobromic acid-acetic acid (1:1) at 0° C. and the mixture was stirred for 15 minutes. To the reaction mixture was added water and was extracted with a mixture of ethyl acetate-hexane. The organic layer was washed with a saturated aqueous solution of sodium bicarbonate and a saturated aqueous solution of sodium chloride successively, dried over anhydrous sodium sulfate and was concentrated. The residue was washed with cooled hexane to give the title compound (27.4 g) having the following physical data.

Aufarbeitung

  1. stirringthe mixture was stirred for 20 minutes
  2. stirringthe mixture was stirred for another 2 hours
  3. additionThereto was added
  4. stirringthe mixture was stirred for 15 minutes
  5. extractionwas extracted with a mixture of ethyl acetate-hexane
  6. washThe organic layer was washed with a saturated aqueous solution of sodium bicarbonate
  7. dry with materiala saturated aqueous solution of sodium chloride successively, dried over anhydrous sodium sulfate
  8. concentrationwas concentrated
  9. washThe residue was washed with cooled hexane

Quellen und Nachweise

ORD-Eintrag
ord-d08d6bc59e7b400e8a04896dcd138cfd
Quelldatensatz
uspto-grants-2006_03
Patentnummer
US07008938B2

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