Water → benzyl (S)-2-(morpholin-4-yl)propionate

HRID 2068867

Reaktionsgleichung

Reaktionsgleichung von HRID 2068867
S(C1C=CC(C)=CC=1)(O)(=O)=O.[CH2:12]([O:19][C:20](=[O:24])[C@H:21]([CH3:23])[NH2:22])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(N(CC)CC)C.Br[CH2:33][CH2:34][O:35][CH2:36][CH2:37]Br.O>CS(C)=O.C(OCC)(=O)C>[N:22]1([C@@H:21]([CH3:23])[C:20]([O:19][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)=[O:24])[CH2:37][CH2:36][O:35][CH2:34][CH2:33]1

Komponenten

7

Edukt 4

HCID 962WaterHCID 8471TriethylamineHCID 21521Bis(2-bromoethyl) etherHCID 2802424L-Alanine, phenylmethyl ester, 4-methylbenzenesulfonate (1:1)

Produkt 1

HCID 13765076benzyl (S)-2-(morpholin-4-yl)propionateAusbeute 66,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 679Dimethyl SulfoxideLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under an argon atmosphere, to a solution of L-alanine benzyl ester tosylate (3.4 g, 9.7 mmol) and triethylamine (6.8 ml) in dimethyl sulfoxide (17 ml) was added a solution of 1-bromo-2-(2-bromoethoxy)ethane (1.5 ml, 12 mmol) in dimethyl sulfoxide (3 ml) under ice-cooling, and the mixture was stirred at room temperature for 24 hr. To the reaction solution were added water and ethyl acetate, and the organic layer was separated. Then, the organic layer was washed with saturated brine, and dried over sodium sulfate. Sodium sulfate was removed by filtration, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography to give the title compound (1.6 g, yield 64%).

Aufarbeitung

  1. temperaturecooling
  2. customthe organic layer was separated
  3. washThen, the organic layer was washed with saturated brine
  4. dry with materialdried over sodium sulfate
  5. customSodium sulfate was removed by filtration
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-7884a18d246b471885497e6efe81cae2
Quelldatensatz
uspto-grants-2012_10
Patentnummer
US08299070B2

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