1,8-Diazabicyclo(5.4.0)undec-7-ene → HCID 140397795、化合物

HRID 1859186ノート

反応式

HRID 1859186 の反応式
[C:1]([O:5][C:6]([NH:8][C:9]([C:11]1[CH:28]=[CH:27][C:14]([O:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][NH:22][C:21](=[O:25])[C:20]2=[O:26])=[CH:13][CH:12]=1)=[NH:10])=[O:7])([CH3:4])([CH3:3])[CH3:2].[N:29]1[CH:34]=[CH:33][CH:32]=[C:31]([CH:35]=[CH:36][C:37]([O:39][CH:40]([C:47]2[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=2)[C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[O:38])[CH:30]=1.N12CCCN=C1CCCCC2>CN(C)C=O>[C:1]([O:5][C:6]([NH:8][C:9]([C:11]1[CH:28]=[CH:27][C:14]([O:15][CH2:16][CH2:17][CH2:18][N:19]2[CH2:24][CH2:23][N:22]([CH:35]([C:31]3[CH:30]=[N:29][CH:34]=[CH:33][CH:32]=3)[CH2:36][C:37]([O:39][CH:40]([C:41]3[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=3)[C:47]3[CH:48]=[CH:49][CH:50]=[CH:51][CH:52]=3)=[O:38])[C:21](=[O:25])[C:20]2=[O:26])=[CH:13][CH:12]=1)=[NH:10])=[O:7])([CH3:4])([CH3:2])[CH3:3]

参加物

5

反応物 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 54425842HCID 54425842、化合物HCID 140397783HCID 140397783、化合物

生成物 1

HCID 140397795HCID 140397795、化合物収率 51.8%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

In 7.5 ml of N,N-dimethylformamide was dissolved 2.5 g of 4-[3-(4-tert-butoxycarbonylamidinophenoxy)propyl]-2,3-dioxopiperazine, and to the solution were added 6.1 g of diphenylmethyl 3-(3-pyridyl)acrylate and 0.48 ml of 1,8-diazabicyclo[5.4.0]undec-7-ene. The resulting mixture was stirred overnight at room temperature and distilled under reduced pressure to remove the solvent. To the resulting residue were added 80 ml of ethyl acetate and 60 ml of water and the pH was adjusted to 7 with 2N hydrochloric acid. The organic layer was separated, washed with water and then a saturated aqueous sodium chloride solution, and then distilled under reduced pressure to remove the solvent. The resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol 20:1) to obtain 2.34 g of diphenylmethyl 3-[4-[3-(4-tert-butoxycarbonylamidinophenoxy)propyl]-2,3-dioxopiperazin-1-yl]-3-(pyridin-3-yl)propionate as a colorless oil.

後処理

  1. distillationdistilled under reduced pressure
  2. customto remove the solvent
  3. additionTo the resulting residue were added 80 ml of ethyl acetate and 60 ml of water
  4. customThe organic layer was separated
  5. washwashed with water
  6. distillationa saturated aqueous sodium chloride solution, and then distilled under reduced pressure
  7. customto remove the solvent
  8. customThe resulting residue was purified by a silica gel column chromatography (eluent; chloroform:methanol 20:1)

出典と根拠

ORDレコード
ord-03efb4e18baa49baaa2feb9640d748d0
出典データセット
uspto-grants-2000_11
特許番号
US06153613

反応ノート

読み込み中…