Chlorosuccinimide → HCID 86729669, compound

HRID 2282993Notes

Reaction equation

[OH:1][N:2]=[CH:3][C:4]1[N:5]=[C:6]([CH:9]2[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]2)[S:7][CH:8]=1.ClN1C(=O)CCC1=O.[F:30][C:31]1[C:36]([CH:37]=[CH2:38])=[C:35]([F:39])[CH:34]=[CH:33][C:32]=1[OH:40].C(=O)([O-])O.[K+]>C(OCC)(=O)C.O>[F:30][C:31]1[C:32]([OH:40])=[CH:33][CH:34]=[C:35]([F:39])[C:36]=1[CH:37]1[O:1][N:2]=[C:3]([C:4]2[N:5]=[C:6]([CH:9]3[CH2:10][CH2:11][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:13][CH2:14]3)[S:7][CH:8]=2)[CH2:38]1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of tert-butyl 4-{4-[(hydroxyimino)methyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (1.278 g) in ethyl acetate (80 ml) was added, at room temperature, N-chlorosuccinimide (658 mg). After stirring at 60° C. for 30 min, 2,4-difluoro-3-vinylphenol (705 mg), potassium hydrogencarbonate (822 mg) and then one drop of water were added, at room temperature, to the reaction mixture. After stirring overnight at room temperature, the reaction mixture was admixed with ethyl acetate and water and extracted with ethyl acetate. The organic extracts were dried over sodium sulphate and concentrated under reduced pressure. The residue was purified by chromatography. This gave tert-butyl 4-{4-[5-(2,6-difluoro-3-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (658 mg).

Workup

stirringAfter stirring overnight at room temperature
extractionextracted with ethyl acetate
dry with materialThe organic extracts were dried over sodium sulphate
concentrationconcentrated under reduced pressure
customThe residue was purified by chromatography

Sources & evidence

ORD record: ord-b7d4197d15484256b24ecb4d904333c9
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09144238B2

Reaction notes

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