Triethylamine → HCID 131711702, Verbindung

HRID 2052274Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2052274
[NH2:1][C@H:2]([C:6]([NH:8][C@H:9]([C:14]([NH:16][C@@H:17]([C:24]([NH2:26])=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH2:10][C:11](=[O:13])[OH:12])=[O:7])[CH2:3][CH2:4][CH3:5].Cl.[NH:28]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C@H:29]([C:40](ON1C(=O)CCC1=O)=[O:41])[CH2:30][C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1.C(N(CC)CC)C>CN(C=O)C>[NH:28]([C:50]([O:52][C:53]([CH3:56])([CH3:55])[CH3:54])=[O:51])[C@H:29]([C:40]([NH:1][C@H:2]([C:6]([NH:8][C@H:9]([C:14]([NH:16][C@@H:17]([C:24]([NH2:26])=[O:25])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)=[O:15])[CH2:10][C:11](=[O:12])[OH:13])=[O:7])[CH2:3][CH2:4][CH3:5])=[O:41])[CH2:30][C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 98767Boc-Trp-OSuHCID 131711703HCID 131711703, Verbindung

Produkt 1

HCID 131711702HCID 131711702, VerbindungAusbeute 66,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

1.50 g (3.74 mmoles) of H-Nva-Asp-D-Phg-NH2.HCl are reacted with 1.50 g (3.74 mmoles) of BOC-Trp-OSu in 30 ml of DMF in the presence of 1.05 ml (7.5 mmoles) of triethylamine. Next day the reaction mixture is evaporated in vacuo, the residue is admixed with water, and the mixture is filtered. The obtained crude product, weighing 2.36 g, is recrystallized from 300 ml of 80% ethanol. 1.54 g (66.2%) of BOC-Trp-Nva-Asp-D-Phg-NH2 are obtained; m.p.: 240° C. (decomposition), Rf5 :0.35, [α]D :-60.5° (c: 1.0, in dimethyl formamide).

Aufarbeitung

  1. customNext day the reaction mixture is evaporated in vacuo
  2. filtrationthe mixture is filtered
  3. customThe obtained crude product
  4. customis recrystallized from 300 ml of 80% ethanol

Quellen und Nachweise

ORD-Eintrag
ord-a158547135d84688860622d6ba4f49db
Quelldatensatz
uspto-grants-1980_01
Patentnummer
US04183909

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