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

HRID 43922Notes

Reaction equation

HRID 43922 reaction equation
[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:12][NH:11][C@H:10]1[CH2:13][CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2].Br[C:16]1[S:17][C:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:19]([CH3:21])[N:20]=1.C(N(C(C)C)CC)(C)C>>[C:1]([O:5][C:6]([NH:8][C@H:9]1[CH2:12][N:11]([C:16]2[S:17][C:18]([C:22]([O:24][CH2:25][CH3:26])=[O:23])=[C:19]([CH3:21])[N:20]=2)[C@H:10]1[CH2:13][CH3:14])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylateHCID 86648820cis(+/-)-3-(tert-Butoxycarbonyl)amino-2-ethylazetidine

Product 1

HCID 86648821Ethyl cis(+/-)-2-{3-[(tert-butoxycarbonyl)amino]-2-ethylazetidin-1-yl}-4-methyl-1,3-thiazole-5-carboxylateYield 84%

Procedure

The same operation as in Example (232c) was performed using cis(±)-3-(tert-butoxycarbonyl)amino-2-ethylazetidine obtained in Example (235f) (66 mg, 0.33 mmol), ethyl 2-bromo-4-methylthiazole-5-carboxylate (82 mg, 0.33 mmol) and diisopropylethylamine (0.12 mL, 0.66 mmol), to obtain 102 mg of the title compound as a white solid (84%).

Sources & evidence

ORD record
ord-6175dce14c034dddaa11c10aeee4641a
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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