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

반응식

HRID 57325 반응식
[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

참가 물질

8

반응물 4

HCID 31398ChlorosuccinimideHCID 1354422-EthenylphenolHCID 516893Potassium BicarbonateHCID 86657567Tert-butyl 4-(4-[(hydroxyimino)methyl]-1,3-thiazol-2-yl)piperidine-1-carboxylate

생성물 1

HCID 66584968Tert-butyl 4-[4-[5-(2-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl]piperidine-1-carboxylate

시약·촉매·용매 3

HCID 962Water촉매HCID 962Water용매HCID 8857Ethyl Acetate용매2회

반응 조건

온도
60 °C

실험 절차

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)

후처리

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

출처 및 근거

ORD 기록
ord-421038e2ed1348cba66ecae6abb876b3
출처 데이터셋
uspto-grants-2016_09
특허 번호
US09434723B2

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