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Triethylamine → (2S,3R)-N-cyclopropyl-3-propyl-2-oxiranecarboxamide

HRID 1173767
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1173767
[CH2:1]([C@H:4]1[O:6][C@@H:5]1[C:7]([OH:9])=O)[CH2:2][CH3:3].C(N(CC)CC)C.C(OC(Cl)=O)C.[CH:23]1([NH2:26])[CH2:25][CH2:24]1>O1CCCC1>[CH:23]1([NH:26][C:7]([C@@H:5]2[C@@H:4]([CH2:1][CH2:2][CH3:3])[O:6]2)=[O:9])[CH2:25][CH2:24]1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 69828CyclopropylamineHCID 11170987HCID 11170987, Verbindung

Produkt 1

HCID 24855930(2S,3R)-N-cyclopropyl-3-propyl-2-oxiranecarboxamideAusbeute 76 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
3×

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

(2S,3R)-3-Propyl-2-oxiranecarboxylic acid (118 mg, 0.8 mmol), triethylamine (0.8 mmol) and tetrahydrofuran (2 ml) were mixed, and the mixture was cooled to −20° C. A tetrahydrofuran solution (1 ml) of ethoxycarbonyl chloride (86 mg, 0.8 mmol) was gradually added, and the mixture was stirred at the same temperature for 30 minutes. A tetrahydrofuran solution (1 ml) of cyclopropylamine (48 mg, 0.8 mmol) was gradually added dropwise, and the mixture was stirred at the same temperature for 2 hours and at room temperature for 2 hours. After the reaction was quenched with water (10 ml), ethyl acetate (10 ml) was added and the solvent was evaporated away under reduced pressure. The mixture was extracted with ethyl acetate (10 ml), and washed with water (5 ml). The solvent was evaporated away under reduced pressure to obtain the title compound as a colorless oil (0.10 g, yield: 76%).

Aufarbeitung

  1. stirringthe mixture was stirred at the same temperature for 2 hours and at room temperature for 2 hours
  2. customAfter the reaction was quenched with water (10 ml), ethyl acetate (10 ml)
  3. additionwas added
  4. customthe solvent was evaporated away under reduced pressure
  5. extractionThe mixture was extracted with ethyl acetate (10 ml)
  6. washwashed with water (5 ml)
  7. customThe solvent was evaporated away under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-626224b7b73f4b84b19d888ca068bd7c
Quelldatensatz
uspto-grants-2010_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07834190B2

Notizen zur Reaktion

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