Chlorosuccinimide → Tert-butyl 4-[4-[5-(2-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidine-1-carboxylate

HRID 57325

反応式

[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.[CH:22]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[OH:30])=[CH2:23].C(=O)([O-])O.[K+].ClN1C(=O)CCC1=O>C(OCC)(=O)C.O>[OH:30][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=1[CH:22]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)[CH2:23]1

参加物

反応条件

温度: 60 °C

実験手順

To a solution of tert-butyl 4-{4-[(hydroxyimino)methyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (3.46 g) and 2-vinylphenol (1.60 g) in ethyl acetate (50 ml) were added, at room temperature, potassium hydrogencarbonate (5.55 g) and N-chlorosuccinimide (1.78 g), and then one drop of water. After stirring at 60° C. overnight, ethyl acetate and water were added to the reaction mixture, which was 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-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (1.70 g)

後処理

extractionwas extracted with ethyl acetate
dry with materialThe organic extracts were dried over sodium sulphate
concentrationconcentrated under reduced pressure
customThe residue was purified by chromatography

出典と根拠

ORDレコード: ord-421038e2ed1348cba66ecae6abb876b3
出典データセット: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US09434723B2

反応式

参加物

反応物 4

生成物 1

試薬・触媒・溶媒 3

反応条件

実験手順

後処理

出典と根拠

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