Potassium Carbonate → Tert-butyl 3-(3-(benzyloxycarbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate

HRID 2362980ノート

反応式

HRID 2362980 の反応式
Cl[C:2]1[CH:24]=[CH:23][C:5]2[N:6]([CH:10]3[CH2:15][CH2:14][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[O:17])[CH2:12][CH2:11]3)[C:7](=O)[NH:8][C:4]=2[CH:3]=1.Cl[CH2:26][C:27]1[CH:28]=[C:29]([CH:40]=[CH:41][CH:42]=1)[C:30]([O:32][CH2:33][C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:31].[C:43](=O)([O-])[O-:44].[K+].[K+]>CN(C)C=O>[CH2:33]([O:32][C:30]([C:29]1[CH:28]=[C:27]([CH:42]=[CH:41][CH:40]=1)[CH2:26][N:8]1[C:43](=[O:44])[C:10]2([CH2:11][CH2:12][N:13]([C:16]([O:18][C:19]([CH3:22])([CH3:20])[CH3:21])=[O:17])[CH2:14][CH2:15]2)[N:6]([C:5]2[CH:23]=[CH:24][CH:2]=[CH:3][CH:4]=2)[CH2:7]1)=[O:31])[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 23024778Benzyl 3-(chloromethyl)benzoateHCID 66652167tert-butyl 4-(5-chloro-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidine-1-carboxylate

生成物 1

HCID 66652022Tert-butyl 3-(3-(benzyloxycarbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate収率 85.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
65 °C

実験手順

A mixture of tert-butyl 4-(5-chloro-2-oxo-2,3-dihydro-1H-benzo[d]imidazol-1-yl)piperidine-1-carboxylate (637 mg, 1.923 mmol, 1 equiv), benzyl 3-(chloromethyl)benzoate (500 mg, 1.923 mmol, 1 equiv) and potassium carbonate (797.3 mg, 5.769 mmol, 3 equiv) in N,N-dimethylformamide was heated at 65° C. for 16 h. The reaction was partitioned between ethyl acetate and water. The organic layer was further washed with brine, dried over MgSO4, filtered and concentrated in vacuo. The resulting residue was purified using the Biotage flash chromatography system (SNAP, 50 g cartridge, Rf=0.4, gradient—5%-30% ethyl acetate in hexanes) to afford the tert-butyl 3-(3-(benzyloxycarbonyl)benzyl)-4-oxo-1-phenyl-1,3,8-triazaspiro[4.5]decane-8-carboxylate as an oil (913 mg, 85.6%). MS for C33H37N3O5 m/z 556.27 (M+H)+.

後処理

  1. customThe reaction was partitioned between ethyl acetate and water
  2. washThe organic layer was further washed with brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified

出典と根拠

ORDレコード
ord-630007a94e9d4a50bd4f43c4584aa3c8
出典データセット
uspto-grants-2014_04
特許番号
US08691836B2

反応ノート

読み込み中…