4-Methylmorpholine → trans 3-(Acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxamide

HRID 5396

Reaktionsgleichung

Reaktionsgleichung von HRID 5396
[C:1]([S:4][CH2:5][C@H:6]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]([C:16](O)=[O:17])[NH:8][C:7]1=[O:19])(=[O:3])[CH3:2].C[N:21]1CCOCC1.ClC(OCC)=O>O1CCCC1.C(Cl)Cl>[C:1]([S:4][CH2:5][C@H:6]1[CH2:15][CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][C@H:9]([C:16]([NH2:21])=[O:17])[NH:8][C:7]1=[O:19])(=[O:3])[CH3:2]

Komponenten

6

Edukt 3

HCID 79724-MethylmorpholineHCID 10928Ethyl chloroformateHCID 86747202trans 3-(Acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid

Produkt 1

HCID 86747204trans 3-(Acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6344DichloromethaneLösungsmittelHCID 8028TetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
-20 °C

Versuchsvorschrift

Trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxylic acid (0.30 g, 1.05 mmol) is dissolved in tetrahydrofuran (5.0 mL). 4-Methylmorpholine (0.14 mL, 1.05 mmol) is then added, and the reaction is cooled to -20° C. Ethyl chloroformate (0.1 mL, 1.05 mmol) is then added, and the reaction is stirred at -20° C. for 30 minutes. The reaction is then filtered, and the filtrate is concentrated to give a yellow oil. This oil is dissolved in methylene chloride (20.0 mL), and anhydrous ammonia gas is bubbled through the solution for 1 hour. The bubbling is stopped, and the reaction is stirred an additional 1 hour. The solvent is evaporated, and the residue is partitioned between ethyl acetate and water. The aqueous layer is extracted several times with ethyl acetate, the combined organic layers are dried (Na2SO4), and the solvent is evaporated to give trans 3-(acetylthiomethyl)-2-oxo-1-azacyclodecane-10-carboxamide, MS:M+1=287.

Aufarbeitung

  1. filtrationThe reaction is then filtered
  2. concentrationthe filtrate is concentrated
  3. customto give a yellow oil
  4. customanhydrous ammonia gas is bubbled through the solution for 1 hour
  5. stirringthe reaction is stirred an additional 1 hour
  6. customThe solvent is evaporated
  7. customthe residue is partitioned between ethyl acetate and water
  8. extractionThe aqueous layer is extracted several times with ethyl acetate
  9. dry with materialthe combined organic layers are dried (Na2SO4)
  10. customthe solvent is evaporated

Quellen und Nachweise

ORD-Eintrag
ord-6d7f78a9e4854515844933e38954e2d1
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05244889

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