4-Methylmorpholine → 1-[3-(4-Cyano-phenyl)propionyl]-6-phenylsulphonamido-1,2,3,4-tetrahydro-quinoline

HRID 379679ノート

反応式

HRID 379679 の反応式
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]([CH3:13])C(O)=O)=[CH:5][CH:4]=1)#[N:2].CN1CC[O:18][CH2:17]C1.ClC(OCC(C)C)=O.[C:29]1([S:35]([NH:38][C:39]2[CH:40]=[C:41]3[C:46](=[CH:47][CH:48]=2)[NH:45][CH2:44][CH2:43][CH2:42]3)(=[O:37])=[O:36])[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>O1CCCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:13][C:17]([N:45]2[C:46]3[C:41](=[CH:40][C:39]([NH:38][S:35]([C:29]4[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=4)(=[O:37])=[O:36])=[CH:48][CH:47]=3)[CH2:42][CH2:43][CH2:44]2)=[O:18])=[CH:7][CH:8]=1)#[N:2]

参加物

6

反応物 4

HCID 79724-MethylmorpholineHCID 62365Isobutyl chloroformateHCID 110335346-Phenylsulphonamido-1,2,3,4-tetrahydro-quinolineHCID 225698632-(4-Cyanophenyl)propanoic acid

生成物 1

HCID 111023311-[3-(4-Cyano-phenyl)propionyl]-6-phenylsulphonamido-1,2,3,4-tetrahydro-quinoline

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-35 °C

実験手順

4.6 g 3-(4-cyano-phenylpropionic acid are dissolved with 2.8 g of N-methyl-morpholine in 120 ml of tetrahydrofuran and cooled to −35° C. To this solution are added 3.6 ml of isobutyl chloroformate, stirring is continued for half an hour and then at −40° C. 7.2 g of 6-phenylsulphonamido-1,2,3,4-tetrahydro-quinoline are added (see Example IV). After 2 hours the solution is slowly allowed to come back to ambient temperature and stirring is continued overnight. Then it is concentrated by evaporation and the residue is taken up in ethyl acetate and water. The organic phase is again washed with water, dried and concentrated by evaporation. The oil remaining is chromatographed over a silica gel column with ethyl acetate/petroleum ether (7:3).

後処理

  1. waitis continued for half an hour
  2. customat −40° C
  3. customto come back to ambient temperature
  4. stirringstirring
  5. waitis continued overnight
  6. concentrationThen it is concentrated by evaporation
  7. washThe organic phase is again washed with water
  8. customdried
  9. concentrationconcentrated by evaporation
  10. customThe oil remaining is chromatographed over a silica gel column with ethyl acetate/petroleum ether (7:3)

出典と根拠

ORDレコード
ord-0b39e586aeb84bb09fdd97e72d4a11f4
出典データセット
uspto-grants-2001_10
特許番号
US06300342B1

反応ノート

読み込み中…