Trifluoroacetic acid → 1,3-Dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione

HRID 1715784ノート

反応式

HRID 1715784 の反応式
[CH2:1]([N:8]1[C@@H:12]([CH2:13][SH:14])[C@H:11]([C:15](O)=[O:16])[N:10]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]1=[O:25])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)(Cl)Cl.N1C=CC=CC=1>[CH2:1]([N:8]1[C@H:12]2[CH2:13][S:14][C:15](=[O:16])[C@H:11]2[N:10]([CH2:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:9]1=[O:25])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

参加物

6

反応物 3

HCID 6422Trifluoroacetic acidHCID 10868DicyclohexylcarbodiimideHCID 11360281(4R,5R)-1,3-dibenzyl-2-oxo-5-(mercaptomethyl)imidazolidin-4-carboxylic acid

生成物 1

HCID 1198171,3-Dibenzyltetrahydro-1H-thieno[3,4-d]imidazole-2,4-dione収率 74.8%

試薬・触媒・溶媒 2

HCID 1049Pyridine溶媒HCID 6212Chloroform溶媒2 回

反応条件

温度
50 °C

実験手順

To 240 ml of a chloroform solution containing 30 g of (4R,5R)-1,3-dibenzyl-2-oxo-5-(mercaptomethyl)imidazolidin-4-carboxylic acid, 22.7 g of pyridine and 2.6 ml of trifluoroacetic acid was added dropwise 60 ml of a chloroform solution containing 17.4 g of dicyclohexylcarbodiimide at 5° C. over 30 minutes. After the solution was refluxed for 5 hours, it was concentrated under reduced pressure. The concentrate was dissolved in ethyl acetate and concentrated, and after the procedure was repeated, 300 ml of ethyl acetate was added to the residue, and the mixture was stirred at 50° C. for 30 minutes. After cooling to 25° C., insoluble materials were filtered off. After the filtrate was concentrated, 85 ml of methanol was added to the concentrate and the mixture was dissolved under heating. After cooling the solution, precipitated crystal was collected by filtration, and washed with cold methanol. Precipitated crystal was dried by blowing air at 50° C. to give 21.3 g of (3aS,6aR)-1,3-dibenzyl-hexahydro-4H-thieno[3,4-d]imidazol-2,4-dione as colorless crystal.

後処理

  1. temperatureAfter the solution was refluxed for 5 hours
  2. concentrationit was concentrated under reduced pressure
  3. dissolutionThe concentrate was dissolved in ethyl acetate
  4. concentrationconcentrated
  5. addition300 ml of ethyl acetate was added to the residue
  6. temperatureAfter cooling to 25° C.
  7. filtrationinsoluble materials were filtered off
  8. concentrationAfter the filtrate was concentrated
  9. addition85 ml of methanol was added to the
  10. concentrationconcentrate
  11. dissolutionthe mixture was dissolved
  12. temperatureunder heating
  13. temperatureAfter cooling the solution
  14. customprecipitated crystal
  15. filtrationwas collected by filtration
  16. washwashed with cold methanol
  17. customPrecipitated crystal
  18. customwas dried
  19. customat 50° C.

出典と根拠

ORDレコード
ord-6dfcc08c68cf49e1bd3b1ad019db3d5f
出典データセット
uspto-grants-2010_09
特許番号
US07799929B2

反応ノート

読み込み中…