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

HRID 43876

Reaction equation

[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:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:17]([CH3:19])[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:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:17]([CH3:19])[N:18]=2)[CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

Reactant 3

HCID 81531Diisopropylethylamine

HCID 15194053-Aminoazetidine, 3-BOC protected

HCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylate

Product 1

HCID 67549080Ethyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl}-4-methyl-1,3-thiazole-5-carboxylateYield 45%

Procedure

The same operation as in Example (217a) was performed using 3-tert-butoxycarbonylaminoazetidine (300 mg, 1.74 mmol), ethyl 2-bromo-4-methylthiazole-5-carboxylate (479 mg, 1.92 mmol) and diisopropylethylamine (0.61 mL, 3.48 mmol), to obtain 265 mg of the title compound as a pale yellow solid (45%).

Sources & evidence

ORD record: ord-fe06294215cc4dce94c4bcc4b79fd9b9
Source dataset: uspto-grants-2013_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08536197B2

Linked notes

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