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Dichloromethane → HCID 178427478, Verbindung

HRID 64828
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 64828
C(Cl)Cl.[S:4]([NH:14][C@H:15]([C:22]([OH:24])=O)[CH2:16][C:17]1[N:21]=[CH:20][NH:19][CH:18]=1)([C:7]1[CH:13]=[CH:12][C:10]([CH3:11])=[CH:9][CH:8]=1)(=[O:6])=[O:5].Cl.[CH2:26]([O:33][C:34](=[O:40])[C@@H:35]1[CH2:39][CH2:38][CH2:37][NH:36]1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C1CCC(N=C=NC2CCCCC2)CC1>C(N(CC)CC)C>[CH2:26]([O:33][C:34](=[O:40])[C@@H:35]1[CH2:39][CH2:38][CH2:37][N:36]1[C:22](=[O:24])[C@H:15]([CH2:16][C:17]1[N:21]=[CH:20][NH:19][CH:18]=1)[NH:14][S:4]([C:7]1[CH:8]=[CH:9][C:10]([CH3:11])=[CH:12][CH:13]=1)(=[O:5])=[O:6])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1
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Komponenten

6

Edukt 4

HCID 6344DichloromethaneHCID 10868DicyclohexylcarbodiimideHCID 2733413Proline benzyl ester hydrochlorideHCID 178427479HCID 178427479, Verbindung

Produkt 1

HCID 178427478HCID 178427478, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8471
Triethylamine
Lösungsmittel

Versuchsvorschrift

To 100 ml of desiccated methylene chloride were added 10 g of Nα -t-butyloxycarbonyl-Nim -tosyl-L-histidine (47) and 6.50 g of L-proline benzyl ester hydrochloride and the mixture was cooled in an ice bath. After adding thereto 2.72 g of triethylamine, 6.05 g of DCC was further added to the mixture and the resultant mixture was stirred for 30 minutes in an ice-bath and stirred overnight at room temperature. Insoluble matters were filtered off and the filtrate was concentrated. The residue thus formed was purified by silica gel column chromatography. By eluting the product with ethyl acetate-benzene (1:1), 13.5 g of Nα -t-butyloxycarbonyl-Nim -tosyl-L-histidyl-L-proline benzyl ester (49) was obtained.

Aufarbeitung

  1. temperaturethe mixture was cooled in an ice bath
  2. additionAfter adding
  3. filtrationInsoluble matters were filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe residue thus formed
  6. customwas purified by silica gel column chromatography
  7. washBy eluting the product with ethyl acetate-benzene (1:1)

Quellen und Nachweise

ORD-Eintrag
ord-de8824e26554475980cfd6cfdeceb05a
Quelldatensatz
uspto-grants-1986_09
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US04610821

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