Chlorosuccinimide → tert-Butyl 4-{4-[5-(2-chloro-6-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

HRID 38738

反応式

HRID 38738 の反応式
[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.ClN1C(=O)CCC1=O.[Cl:30][C:31]1[C:32]([CH:38]=[CH2:39])=[C:33]([OH:37])[CH:34]=[CH:35][CH:36]=1.C(=O)([O-])O.[K+]>C(OCC)(=O)C.O>[Cl:30][C:31]1[CH:36]=[CH:35][CH:34]=[C:33]([OH:37])[C:32]=1[CH:38]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)[CH2:39]1

参加物

8

反応物 4

HCID 31398ChlorosuccinimideHCID 516893Potassium BicarbonateHCID 189709553-Chloro-2-vinylphenolHCID 86657567Tert-butyl 4-(4-[(hydroxyimino)methyl]-1,3-thiazol-2-yl)piperidine-1-carboxylate

生成物 1

HCID 67244553tert-Butyl 4-{4-[5-(2-chloro-6-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate

試薬・触媒・溶媒 3

HCID 962Water触媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒2 回

実験手順

To a solution of tert-butyl 4-{4-[(hydroxyimino)methyl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (400 mg) in ethyl acetate (10 ml) was added N-chlorosuccinimide (206 mg). The reaction mixture is stirred at reflux for 30 min. To the reaction mixture were added 3-chloro-2-vinylphenol (397 mg) and potassium hydrogencarbonate (257 mg) at room temperature, and then one drop of water. After stirring at room temperature overnight, 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-chloro-6-hydroxyphenyl)-4,5-dihydro-1,2-oxazol-3-yl]-1,3-thiazol-2-yl}piperidine-1-carboxylate (345 mg).

後処理

  1. temperatureat reflux for 30 min
  2. stirringAfter stirring at room temperature overnight
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic extracts were dried over sodium sulphate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by chromatography

出典と根拠

ORDレコード
ord-ac0a7783ad7e4fc3967ed391fe24bd19
出典データセット
uspto-grants-2013_09
特許番号
US08524743B2

関連ノート

読み込み中…