3,3-Dimethylbutanoyl chloride → N-[N-[N-(3,3-dimethylbutyryl)-L-leucyl]-D-tryptophanyl]-beta-alanine ethyl ester

HRID 2295173Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2295173
[NH2:1][C@H:2]([C:7]([NH:9][C@@H:10]([C:21]([NH:23][CH2:24][CH2:25][C:26]([O:28][CH2:29][CH3:30])=[O:27])=[O:22])[CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)=[O:8])[CH2:3][CH:4]([CH3:6])[CH3:5].FC(C(O)=O)(F)F.[CH3:38][C:39]([CH3:45])([CH3:44])[CH2:40][C:41](Cl)=[O:42]>N1C=CC=CC=1>[CH2:29]([O:28][C:26](=[O:27])[CH2:25][CH2:24][NH:23][C:21](=[O:22])[C@@H:10]([CH2:11][C:12]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[NH:14][CH:13]=1)[NH:9][C:7](=[O:8])[C@H:2]([CH2:3][CH:4]([CH3:5])[CH3:6])[NH:1][C:41](=[O:42])[CH2:40][C:39]([CH3:45])([CH3:44])[CH3:38])[CH3:30]

Komponenten

4

Edukt 2

HCID 815143,3-Dimethylbutanoyl chlorideHCID 131719107Leu-DTrp-betaAla-OEt-TFA

Produkt 1

HCID 54526361N-[N-[N-(3,3-dimethylbutyryl)-L-leucyl]-D-tryptophanyl]-beta-alanine ethyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 1049PyridineLösungsmittel

Versuchsvorschrift

To a solution of Leu-DTrp-βAla-OEt.TFA (33.0 mg) obtained in Example 51-(1) in pyridine (0.5 ml) was added 3,3-dimethylbutyryl chloride (12.8 ml) at 0° C. under nitrogen. The reaction mixture was stirred for 10 min, quenched with water (0.1 ml), and concentrated under reduced pressure. The residue was purified by preparative TLC (Merck, Kieselgel 60 F254) with chloroform/methanol=15/1 for development to give the product (21.8 mg).

Aufarbeitung

  1. customquenched with water (0.1 ml)
  2. concentrationconcentrated under reduced pressure
  3. customThe residue was purified by preparative TLC (Merck, Kieselgel 60 F254) with chloroform/methanol=15/1 for development

Quellen und Nachweise

ORD-Eintrag
ord-546ac5a1b77a4d058517cad3ca08fbdf
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05691315

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