Diisopropylethylamine → Ethyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl)-4-n-butyl-1,3-thiazole-5-carboxylate

HRID 43880

Reaktionsgleichung

Reaktionsgleichung von HRID 43880
[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:12][NH:11][CH2:10]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:14]1[S:15][C:16]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:17]([CH2:19][CH2:20][CH2:21][CH3:22])[N:18]=1.C(N(C(C)C)CC)(C)C>>[C:1]([O:5][C:6]([NH:8][CH:9]1[CH2:10][N:11]([C:14]2[S:15][C:16]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[C:17]([CH2:19][CH2:20][CH2:21][CH3:22])[N:18]=2)[CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Komponenten

4

Edukt 3

HCID 81531DiisopropylethylamineHCID 15194053-Aminoazetidine, 3-BOC protectedHCID 67549203Ethyl 2-bromo-4-n-butyl-1,3-thiazole-5-carboxylate

Produkt 1

HCID 67548951Ethyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl)-4-n-butyl-1,3-thiazole-5-carboxylateAusbeute 74,4 %

Versuchsvorschrift

The same operation as in Example (217a) was performed using 3-tert-butoxycarbonylaminoazetidine (212 mg, 1.23 mmol), ethyl 2-bromo-4-n-butyl-1,3-thiazole-5-carboxylate obtained in Example (220b) (300 mg, 1.03 mmol) and diisopropylethylamine (0.36 mL, 2.06 mmol), to obtain 294 mg of the title compound as a white solid (74%).

Quellen und Nachweise

ORD-Eintrag
ord-2e2a985ed8fb4f6ba1c706102444b688
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08536197B2

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