Potassium Iodide → HCID 86646926、化合物

HRID 221504ノート

反応式

HRID 221504 の反応式
[C:1]([O:5][C:6]([NH:8][C@H:9]([CH2:29][C:30]1[CH:35]=[C:34]([F:36])[C:33]([F:37])=[CH:32][C:31]=1[F:38])[CH2:10][C:11]([N:13]1[CH2:18][CH2:17][N:16]2[C:19]([C:25]([F:28])([F:27])[F:26])=[N:20][C:21]([C:22]([OH:24])=[O:23])=[C:15]2[CH2:14]1)=[O:12])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:39](=[O:51])([O:44][CH:45]1[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1)[O:40][CH:41](Cl)[CH3:42].[I-].[K+].C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH:45]1([O:44][C:39]([O:40][CH2:41][CH2:42][O:23][C:22]([C:21]2[N:20]=[C:19]([C:25]([F:27])([F:28])[F:26])[N:16]3[CH2:17][CH2:18][N:13]([C:11](=[O:12])[CH2:10][C@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:7])[CH2:29][C:30]4[CH:35]=[C:34]([F:36])[C:33]([F:37])=[CH:32][C:31]=4[F:38])[CH2:14][C:15]=23)=[O:24])=[O:51])[CH2:50][CH2:49][CH2:48][CH2:47][CH2:46]1

参加物

6

反応物 4

HCID 4875Potassium IodideHCID 11430Potassium CarbonateHCID 112295291-Chloroethyl Cyclohexyl CarbonateHCID 59548952(R)-7-[3-tert-butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid2 回

生成物 1

HCID 86646926HCID 86646926、化合物収率 69.4%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

(R)-7-[3-tert-Butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid 2a (0.275 g, 0.5 mmol) and 4 mL of N,N-dimethylformamide were added to the reaction tube. After stirring until 2a was dissolved, 1-chloroethyl cyclohexyl carbonate (0.124 g, 0.6 mmol), potassium iodide (0.0415 g, 0.25 mmol) and potassium carbonate (0.083 g, 0.6 mmol) were then added to the solution successively. Upon completion of the addition, the reaction tube was sealed up. The reaction mixture was reacted at 65° C. in an oil bath for 2 hours and monitored by thin layer chromatography until the disappearance of the starting materials, and then the oil bath was removed. After cooling to room temperature, 40 mL of water was added to the reaction tube. The reaction mixture was extracted with ethyl acetate (30 mL×3). The combined organic phase was washed with 30 mL of water and 30 mL of saturated brine successively. The combined organic phase was dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was purified by silica gel column chromatography to obtain the title compound (R)-7-[3-tert-butoxycarbonylamino-4-(2,4,5-trifluoro-phenyl)-butyryl]-3-trifluoromethyl-5,6,7,8-tetrahydro-imidazo[1,5-a]pyrazine-1-carboxylic acid (1-cyclohexyloxycarbonyloxy)-ethyl ester 38a (0.25 g, yield 69.4%) as a white solid.

後処理

  1. dissolutionwas dissolved
  2. additionUpon completion of the addition
  3. customthe reaction tube was sealed up
  4. customThe reaction mixture was reacted at 65° C. in an oil bath for 2 hours
  5. customthe oil bath was removed
  6. addition40 mL of water was added to the reaction tube
  7. extractionThe reaction mixture was extracted with ethyl acetate (30 mL×3)
  8. washThe combined organic phase was washed with 30 mL of water and 30 mL of saturated brine successively
  9. dry with materialThe combined organic phase was dried over anhydrous magnesium sulfate
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure
  12. customThe resulting residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-85cb416075424d76b600e4793143ce68
出典データセット
uspto-grants-2012_06
特許番号
US08207161B2

反応ノート

読み込み中…