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Dimethylamine, hydrochloride → Tert-butyl 3-(dimethylcarbamoyl)azetidine-1-carboxylate

HRID 1799026
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1799026
[C:1]([O:5][C:6]([N:8]1[CH2:11][CH:10]([C:12]([OH:14])=O)[CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Cl.[CH3:16][NH:17][CH3:18].Cl.CN(C)CCCN=C=NCC.O.ON1C2C=CC=CC=2N=N1>C(OCC)(=O)C.CN(C)C=O.C(N(CC)CC)C>[CH3:16][N:17]([CH3:18])[C:12]([CH:10]1[CH2:11][N:8]([C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[CH2:9]1)=[O:14]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

8

Edukt 4

HCID 10473Dimethylamine, hydrochlorideHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 27559811-Boc-Azetidine-3-carboxylic acidHCID 27960291-Hydroxybenzotriazole hydrate

Produkt 1

HCID 59492610Tert-butyl 3-(dimethylcarbamoyl)azetidine-1-carboxylateAusbeute 40 %

Reagenzien, Katalysatoren, Lösungsmittel

3
HCID 6228DimethylformamideLösungsmittelHCID 8471TriethylamineLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under a nitrogen atmosphere, triethylamine (1.2 ml) was added to a mixture of 1-(t-butyloxycarbonyl)-azetidine-3-carboxylic acid (0.804 g), dimethylamine hydrochloride (0.489 g), 1-(3-dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (0.997 g), 1-hydroxybenzotriazole hydrate (0.796 g), and dimethylformamide (8 ml), and the mixture was stirred at room temperature for 3 days. To the reaction mixture was added ethyl acetate (30 ml), and the mixture was successively washed once with water, once with hydrochloric acid, once with water, twice with saturated aqueous sodium hydrogen carbonate and twice with water. The organic layer was dried over anhydrous sodium sulfate, and filtered. The filtrate was concentrated under reduced pressure to give the title compound (0.364 g, 40%).

Aufarbeitung

  1. washthe mixture was successively washed once with water, once with hydrochloric acid, once with water, twice with saturated aqueous sodium hydrogen carbonate and twice with water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

Quellen und Nachweise

ORD-Eintrag
ord-8ebf69b344834323b6a882b0d4787d9b
Quelldatensatz
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08343994B2

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