Dicyclohexylcarbodiimide → 6-Amidino-2-naphthyl 5-(3-t-butoxycarbonylpropionylaminomethyl)furan-2-carboxylate hydrochloride

HRID 1734103ノート

反応式

HRID 1734103 の反応式
[C:1]([O:8][C:9]([CH3:12])([CH3:11])[CH3:10])(=[O:7])[CH2:2][CH2:3][C:4]([O-:6])=O.[ClH:13].Cl.[NH2:15][CH2:16][C:17]1[O:21][C:20]([C:22]([O:24][C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[C:30]([C:35](=[NH:37])[NH2:36])[CH:31]=3)[CH:26]=2)=[O:23])=[CH:19][CH:18]=1.C1CCC(N=C=NC2CCCCC2)CC1>CN(C1C=CN=CC=1)C.N1C=CC=CC=1>[ClH:13].[C:9]([O:8][C:1]([CH2:2][CH2:3][C:4]([NH:15][CH2:16][C:17]1[O:21][C:20]([C:22]([O:24][C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[C:30]([C:35](=[NH:36])[NH2:37])[CH:31]=3)[CH:26]=2)=[O:23])=[CH:19][CH:18]=1)=[O:6])=[O:7])([CH3:12])([CH3:11])[CH3:10]

参加物

6

反応物 3

HCID 10868DicyclohexylcarbodiimideHCID 22317022Butanedioic acid,1-(1,1-dimethylethyl) esterHCID 22398815HCID 22398815、化合物

生成物 1

HCID 223988046-Amidino-2-naphthyl 5-(3-t-butoxycarbonylpropionylaminomethyl)furan-2-carboxylate hydrochloride収率 68%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 1049Pyridine溶媒

実験手順

To 11.4 g of mono-t-butyl succinate, 23.5 g of 6-amidino-2-naphthyl 5-aminomethylfuran-2-carboxylate dihydrochloride and 0.66 g of DMAP was added 115 ml of pyridine, and the mixture was stirred with ice-cooling. After 10 minutes, 25.6 g of DCC was added and the mixture was stirred for 3 hours while cooling with ice and for 16 hours at room temperature. The precipitated crystals were filtered off, and the filtrate was added in small portions into 2 l of ether and stirred at room temperature for 3 l hours. After removing the supernatant by decantation, 1 l of acetone was added to the residue and stirred for 1 hour. The precipitate was collected by filtration, then dissolved in 60 ml of methanol and 3 g of active carbon was added to the solution. The mixture was stirred for 30 minutes while cooling with ice, then the insolubles were filtered off and the filtrate was added into 1.5 l of acetone. The mixture was stirred for 5 hours while cooling with ice, and the precipitated crystals were collected by filtration to obtain 21 g of the intended product.

後処理

  1. temperaturecooling
  2. stirringthe mixture was stirred for 3 hours
  3. filtrationThe precipitated crystals were filtered off
  4. additionthe filtrate was added in small portions into 2 l of ether
  5. stirringstirred at room temperature for 3 l hours
  6. customAfter removing the supernatant by decantation, 1 l of acetone
  7. additionwas added to the residue
  8. stirringstirred for 1 hour
  9. filtrationThe precipitate was collected by filtration
  10. dissolutiondissolved in 60 ml of methanol
  11. addition3 g of active carbon was added to the solution
  12. stirringThe mixture was stirred for 30 minutes
  13. temperaturewhile cooling with ice
  14. filtrationthe insolubles were filtered off
  15. additionthe filtrate was added into 1.5 l of acetone
  16. stirringThe mixture was stirred for 5 hours
  17. temperaturewhile cooling with ice
  18. filtrationthe precipitated crystals were collected by filtration

出典と根拠

ORDレコード
ord-22d060cde1e242b9bb63d61a2702ae1f
出典データセット
uspto-grants-1996_07
特許番号
US05532267

反応ノート

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