Diisopropylethylamine → Ethyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl)-1,3-benzothiazole-6-carboxylate

HRID 43898Notes

Reaction equation

HRID 43898 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]2[CH:22]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:20]=[CH:19][C:17]=2[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]3[CH:22]=[C:21]([C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:20]=[CH:19][C:17]=3[N:18]=2)[CH2:12]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 3

HCID 81531DiisopropylethylamineHCID 15194053-Aminoazetidine, 3-BOC protectedHCID 12067225Ethyl 2-bromo-6-benzothiazolecarboxylate

Product 1

HCID 67548952Ethyl 2-{3-[(tert-butoxycarbonyl)amino]azetidin-1-yl)-1,3-benzothiazole-6-carboxylateYield 75%

Procedure

The same operation as in Example (221a) was performed using 3-tert-butoxycarbonylaminoazetidine (199 mg, 1.15 mmol), ethyl 2-bromo-1,3-benzothiazole-6-carboxylate obtained in Example (225a) (300 mg, 1.05 mmol) and diisopropylethylamine (0.37 mL, 2.10 mmol), to obtain 297 mg of the title compound as a milk white solid (75%).

Sources & evidence

ORD record
ord-1b5cc856370348be9d1b9e1bd3f1172f
Source dataset
uspto-grants-2013_09
Patent number
US08536197B2

Reaction notes

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