Diisopropylethylamine → tert-Butyl (1R,5R)-6-[5-(ethoxycarbonyl)-4-methyl-1,3-thiazol-2-yl]-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate

HRID 43923Notes

Reaction equation

HRID 43923 reaction equation
[C@@H:1]12[CH2:7][NH:6][C@@H:5]1[CH2:4][CH2:3][N:2]2[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9].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>>[CH2:25]([O:24][C:22]([C:18]1[S:17][C:16]([N:6]2[CH2:7][C@@H:1]3[C@H:5]2[CH2:4][CH2:3][N:2]3[C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])=[N:20][C:19]=1[CH3:21])=[O:23])[CH3:26]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 2824057Ethyl 2-bromo-4-methyl-1,3-thiazole-5-carboxylateHCID 55280127HCID 55280127, compound

Product 1

HCID 86648822tert-Butyl (1R,5R)-6-[5-(ethoxycarbonyl)-4-methyl-1,3-thiazol-2-yl]-2,6-diazabicyclo[3.2.0]heptane-2-carboxylateYield 99.5%

Procedure

The same operation as in Example (217a) was performed using tert-butyl (1R,5R)-2,6-diazabicyclo[3.2.0]heptane-2-carboxylate obtained in Example (236a) (150 mg, 0.76 mmol), ethyl 2-bromo-4-methylthiazole-5-carboxylate (189 mg, 0.76 mmol) and diisopropylethylamine (0.26 mL, 1.51 mmol), to obtain 278 mg of the title compound as a yellow oily substance (100%).

Sources & evidence

ORD record
ord-3d20ce4da56c40ddac012cb6a7e48ff9
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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