Triethylamine → HCID 131711694, Verbindung

HRID 2052271Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2052271
[NH2:1][C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][C@H:18]([C:25]([NH2:27])=[O:26])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:16])[CH2:11][C:12](=[O:14])[OH:13])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].Cl.[NH:29]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[C@H:30]([C:41](ON1C(=O)CCC1=O)=[O:42])[CH2:31][C:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[NH:34][CH:33]=1.C(N(CC)CC)C>CN(C=O)C>[NH:29]([C:51]([O:53][C:54]([CH3:57])([CH3:56])[CH3:55])=[O:52])[C@H:30]([C:41]([NH:1][C@H:2]([C:7]([NH:9][C@H:10]([C:15]([NH:17][C@H:18]([C:25]([NH2:27])=[O:26])[C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)=[O:16])[CH2:11][C:12](=[O:13])[OH:14])=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5])=[O:42])[CH2:31][C:32]1[C:40]2[C:35](=[CH:36][CH:37]=[CH:38][CH:39]=2)[NH:34][CH:33]=1

Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 98767Boc-Trp-OSuHCID 131711695HCID 131711695, Verbindung

Produkt 1

HCID 131711694HCID 131711694, VerbindungAusbeute 65,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

2.2 g (5.3 mmoles) of H-Leu-Asp-L-Phg-NH2.HCl, prepared as described in Example 6, Step 3, are reacted with 2.32 g (5.8 mmoles) of BOC-Trp-OSu in 50 ml of DMF in the presence of 1.48 ml (10.6 mmoles) of triethylamine. Next day the reaction mixture is evaporated in vacuo and the residue is triturated with water. The obtained crude product, weighing 3.30 g, is crystallized from 70 ml of 80% ethanol under decolourizing. 2.30 g (65%) of BOC-Trp-Leu-Asp-L-Phg-NH2 are obtained; m.p.: 205°-207° C. (decomposition), Rf5 : 0.40, [α]D : -7.3° (c: 1.0, in dimethyl formamide).

Aufarbeitung

  1. customNext day the reaction mixture is evaporated in vacuo
  2. customthe residue is triturated with water
  3. customThe obtained crude product
  4. customis crystallized from 70 ml of 80% ethanol

Quellen und Nachweise

ORD-Eintrag
ord-50a81e9881214f4ab0388e49fed11b64
Quelldatensatz
uspto-grants-1980_01
Patentnummer
US04183909

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