1,2-Dibromoethane → methyl (3S)-2,2-dimethylthiomorpholine-3-carboxylate

HRID 1180549Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1180549
Br[CH2:2][CH2:3]Br.Cl.[CH3:6][O:7][C:8](=[O:15])[C@@H:9]([C:11]([SH:14])([CH3:13])[CH3:12])[NH2:10].C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:12][C:11]1([CH3:13])[S:14][CH2:3][CH2:2][NH:10][C@H:9]1[C:8]([O:7][CH3:6])=[O:15]

Komponenten

5

Edukt 3

HCID 78391,2-DibromoethaneHCID 516892Sodium BicarbonateHCID 12278508Methyl 3-mercapto-D-valinate hydrochloride

Produkt 1

HCID 18345630methyl (3S)-2,2-dimethylthiomorpholine-3-carboxylateAusbeute 97 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution of 1,2-dibromoethane (6.77 g, 36 mmol) in dimethylformamide (25 ml) was added, over a period of 30 minutes, a solution of D-penicillamine methyl ester hydrochloride (6 g, 30 mmol) and 1,8-diazobicyclo[5.4.0]undeca-7-ene (13.7 g, 90 mmol) in dimethylformamide (50 ml). The resulting mixture was stirred for 18 hours at room temperature. The reaction mixture was poured into a saturated sodium bicarbonate solution and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and the solvent was removed in vacuo to give 5.5 g (97%) of the product.

Aufarbeitung

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customthe solvent was removed in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-bdc60ec671bf4b129201bb477950fc48
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07282496B2

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