Trifluoroacetic acid → Carbobenzyloxy-L-phenylalanyl-L-leucinamide

Reaktionsgleichung

[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([OH:12])=O)[CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[NH2:23][C@H:24]([C:29]([NH2:31])=[O:30])[CH2:25][CH:26]([CH3:28])[CH3:27].FC(F)(F)C(O)=O>>[NH:1]([C:13]([O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)=[O:14])[C@H:2]([C:10]([NH:23][C@H:24]([C:29]([NH2:31])=[O:30])[CH2:25][CH:26]([CH3:28])[CH3:27])=[O:12])[CH2:3][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=1

Komponenten

Edukt 3

HCID 6422Trifluoroacetic acid

HCID 69640Leucinamide

HCID 70878Benzyloxycarbonyl-L-phenylalanine

Produkt 1

HCID 13386706Carbobenzyloxy-L-phenylalanyl-L-leucinamide

Versuchsvorschrift

30 mg (0.1 mole) Z-Phe-OH and 13 mg (0.1 mmole) Leu-NH2 are placed into an unsealed glass container having a 12 mm inner diameter and stirred with a spatula. Then, a mixture of 161 mg (0.5 mole) Na2 SO4.10H2O and 5 mg thermolysine is added, the glass container is closed and subjected to ultrasonic waves in an ultrasound bath at 40° C. After 20 minutes the reaction is stopped with 0.4 ml 5% (v/v) aqueous trifluoroacetic acid. The analytical evaluation is carried out by means of HPLC and comparison with an authentic specimen.