N-bromobutanimide → Methyl 2-(5-bromo-2-methyl-1,3-thiazol-4-yl)-2-(tert-butoxy)acetate

HRID 591012Notes

Reaction equation

[Br:1]N1C(=O)CCC1=O.[C:9]([O:13][CH:14]([C:19]1[N:20]=[C:21]([CH3:24])[S:22][CH:23]=1)[C:15]([O:17][CH3:18])=[O:16])([CH3:12])([CH3:11])[CH3:10]>CN(C)C=O>[Br:1][C:23]1[S:22][C:21]([CH3:24])=[N:20][C:19]=1[CH:14]([O:13][C:9]([CH3:12])([CH3:11])[CH3:10])[C:15]([O:17][CH3:18])=[O:16]

Participants

Conditions

Temperature: 70 °C

Procedure

Under a nitrogen atmosphere, N-bromosuccinimide (39 mg, 0.22 mmol) was added to a solution of methyl 2-(tert-butoxy)-2-(2-methyl-1,3-thiazol-4-yl)acetate (15c) (50 mg, 0.21 mmol) in N,N-dimethylformamide (4 mL). The reaction mixture was warmed at 70° C. for 30 minutes then concentrated in vacuo. The residue was diluted with ethyl acetate (40 mL) and washed with water (2×20 mL), brine (20 mL), dried over sodium sulfate, filtered and evaporated under reduced pressure to give the desired product as a yellow oil without further purification (70 mg, 0.21 mmol, 100%).

Workup

concentrationthen concentrated in vacuo
additionThe residue was diluted with ethyl acetate (40 mL)
washwashed with water (2×20 mL), brine (20 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-47fe65bfa4df4e749b86ed1184bd5ccd
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238026B2

Reaction notes

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