Ethyl Acetate → Methyl 2-(5-bromo-2-phenyl-1,3-thiazol-4-yl)-2-(tert-butoxy)acetate

HRID 590971Notes

Reaction equation

[Br:1]N1C(=O)CCC1=O.[C:9]([O:13][CH:14]([C:19]1[N:20]=[C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[S:22][CH:23]=1)[C:15]([O:17][CH3:18])=[O:16])([CH3:12])([CH3:11])[CH3:10].C(OCC)(=O)C>CN(C)C=O>[Br:1][C:23]1[S:22][C:21]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[N:20][C:19]=1[CH:14]([O:13][C:9]([CH3:12])([CH3:10])[CH3:11])[C:15]([O:17][CH3:18])=[O:16]

Participants

Conditions

Temperature: 70 °C

Procedure

Under a nitrogen atmosphere, N-bromosuccinimide (108 mg, 0.6 mmol) was added to a solution of methyl 2-(tert-butoxy)-2-(2-phenyl-1,3-thiazol-4-yl)acetate (6b) (30 mg, 0.1 mmol) in N,N-dimethylformamide (2 mL). The reaction mixture was warmed at 70° C. for 3 hours and ethyl acetate (20 mL) was then added. The organic layer was washed with water (2×10 mL), brine (10 mL), dried over sodium sulfate, filtered, and evaporated under reduced pressure. The residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20) to afford the desired product (6c) as a yellow oil (30 mg, 0.078 mmol, 78%).

Workup

washThe organic layer was washed with water (2×10 mL), brine (10 mL)
dry with materialdried over sodium sulfate
filtrationfiltered
customevaporated under reduced pressure
customThe residue was purified by flash chromatography on silica gel (cyclohexane/ethyl acetate 80/20)

Sources & evidence

ORD record: ord-bb6a946b4aee477187a315441bcb4b93
Source dataset: uspto-grants-2016_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09238026B2

Reaction notes

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