Dicyclohexylcarbodiimide → 4-Amidino-2-benzoylphenyl 6-benzyloxycarbonylaminocaproate

HRID 1589474Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1589474
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([OH:19])=[O:18])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:40]1[CH:45]=[CH:44][C:43]([C:46](=[NH:48])[NH2:47])=[CH:42][C:41]=1[C:49](=[O:56])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)(=O)=O>N1C=CC=CC=1>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]([O:19][C:40]1[CH:45]=[CH:44][C:43]([C:46](=[NH:47])[NH2:48])=[CH:42][C:41]=1[C:49](=[O:56])[C:50]1[CH:55]=[CH:54][CH:53]=[CH:52][CH:51]=1)=[O:18])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 10868DicyclohexylcarbodiimideHCID 747586-(((Phenylmethoxy)carbonyl)amino)hexanoic acidHCID 540991824-Amidino-2-benzoylphenol methanesulfonate

Produkt 1

HCID 131784414-Amidino-2-benzoylphenyl 6-benzyloxycarbonylaminocaproateAusbeute 36,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

Into 50 ml of anhydrous pyridine, was dissolved 4.0 g of 6-benzyloxycarbonylaminocaproic acid. To the solution, while being cooled in ice, was added 3.7 g of DCC. After having been stirred for 30 minutes, the mixture was admixed with 5.0 g of 4-amidino-2-benzoylphenol methanesulfonate and stirred overnight at room temperature. The precipitate which was formed was separated by filtration and washed with pyridine. Ethyl ether was added to the filtrate to precipitate white crystals. The crystals were collected by filtration, washed with ethyl ether, dissolved in DMF, and admixed with ethyl ether to precipitate colorless crystals which were collected by filtration and dried to obtain 5.7 g of an anhydrous substance. This substance was recrystallized from ethanol to obtain 2.7 g of colorless needle crystals of 4-amidino 2-benzoylphenyl 6-benzyloxycarbonylaminocaproate methanesulfonate.

Aufarbeitung

  1. temperatureTo the solution, while being cooled in ice
  2. stirringstirred overnight at room temperature
  3. customThe precipitate which was formed
  4. customwas separated by filtration
  5. washwashed with pyridine
  6. additionEthyl ether was added to the filtrate
  7. customto precipitate white crystals
  8. filtrationThe crystals were collected by filtration
  9. washwashed with ethyl ether
  10. dissolutiondissolved in DMF
  11. customto precipitate colorless crystals which
  12. filtrationwere collected by filtration
  13. customdried
  14. customto obtain 5.7 g of an anhydrous substance
  15. customThis substance was recrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-1bd09fd206854865aae7cfb52c38a27e
Quelldatensatz
uspto-grants-1986_02
Patentnummer
US04570006

Notizen zur Reaktion

Wird geladen…