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4-Methylmorpholine → 3-(t butoxycarbonylamino)propionic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide

HRID 18412
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 18412
[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][C:11]([OH:13])=O)=[O:7])([CH3:4])([CH3:3])[CH3:2].CN1CCOCC1.C(Cl)(=O)OCC(C)C.Cl.[C:30]12([CH2:40][CH2:41][NH:42][CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[CH2:39][CH:34]3[CH2:35][CH:36]([CH2:38][CH:32]([CH2:33]3)[CH2:31]1)[CH2:37]2.C(=O)([O-])O.[Na+]>O1CCCC1.C(OCC)(=O)C>[C:30]12([CH2:40][CH2:41][N:42]([CH2:43][CH2:44][CH2:45][CH2:46][CH3:47])[C:11](=[O:13])[CH2:10][CH2:9][NH:8][C:6]([O:5][C:1]([CH3:2])([CH3:3])[CH3:4])=[O:7])[CH2:37][CH:36]3[CH2:35][CH:34]([CH2:33][CH:32]([CH2:38]3)[CH2:31]1)[CH2:39]2
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 5

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 76809N-((1,1-dimethylethoxy)carbonyl)-beta-alanineHCID 516892Sodium BicarbonateHCID 498316802-(1Adamantyl)-n-pentylethylamine hydrochloride

Produkt 1

HCID 57481272
3-(t butoxycarbonylamino)propionic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide
Ausbeute 85,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
-15 °C

Versuchsvorschrift

3-(t-Butoxycarbonylamino)propionic acid (1.0 g, 5.3 mmol) was dissolved in anhydrous tetrahydrofuran (15 ml), N-methylmorpholine (0.6 ml, 5.5 mmol) was added to the solution, the mixture was stirred at −15° C., and isobutyl chlorocarbonate (0.7 ml, 5.4 mmol) was added to the mixture. Then a solution of a free base of 2-(1-adamantyl)-N-pentylethylamine hydrochloride (Intermediate No. 1-1, 1.5 g, 5.3 mmol) in anhydrous tetrahydrofuran (15 ml) was added thereto at −18° C. The whole was stirred at 0° C. for 1.5 hours, then ethyl acetate (100 ml) and a saturated aqueous sodium hydrogencarbonate solution (100 ml) were added to the reaction mixture to distribute it. The organic layer was washed with a 10% aqueous citric acid solution (100 ml), water (100 ml) and a saturated aqueous sodium chloride solution (100 ml) successively, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. Then the obtained concentrate was purified by silica gel column chromatography to give 3-(t-butoxycarbonylamino)propionic acid N-[2-(1-adamantyl)ethyl]-N-pentylamide (1.9 g, 85%) as an oily matter.

Aufarbeitung

  1. customat −18° C
  2. stirringThe whole was stirred at 0° C. for 1.5 hours
  3. washThe organic layer was washed with a 10% aqueous citric acid solution (100 ml), water (100 ml)
  4. dry with materiala saturated aqueous sodium chloride solution (100 ml) successively, dried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. concentrationThen the obtained concentrate
  7. customwas purified by silica gel column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-06d15e2d53eb416cb390949bc4888ced
Quelldatensatz
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07741346B2

Notizen zur Reaktion

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