Fmoc-L-tryptophan → Fmoc-Trp(2Pmc)-OH

HRID 516191

Reaktionsgleichung

N(C(OCC1C2C(=CC=CC=2)C2C1=CC=CC=2)=O)[C@H](C(O)=O)CCCNC(=N)N[S:9]([C:12]1[C:25]([CH3:26])=[C:23]([CH3:24])[C:22]2[O:21][C:18]([CH3:20])([CH3:19])[CH2:17][CH2:16][C:15]=2[C:13]=1[CH3:14])(=[O:11])=[O:10].[NH:48]([C:63]([O:65][CH2:66][CH:67]1[C:79]2[C:74](=[CH:75][CH:76]=[CH:77][CH:78]=2)[C:73]2[C:68]1=[CH:69][CH:70]=[CH:71][CH:72]=2)=[O:64])[C@H:49]([C:60]([OH:62])=[O:61])[CH2:50][C:51]1[C:59]2[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=2)[NH:53][CH:52]=1>C(O)(C(F)(F)F)=O>[NH:48]([C:63]([O:65][CH2:66][CH:67]1[C:68]2[C:73](=[CH:72][CH:71]=[CH:70][CH:69]=2)[C:74]2[C:79]1=[CH:78][CH:77]=[CH:76][CH:75]=2)=[O:64])[C@H:49]([C:60]([OH:62])=[O:61])[CH2:50][C:51]1[C:59]2[C:54](=[CH:55][CH:56]=[CH:57][CH:58]=2)[NH:53][C:52]=1[S:9]([C:12]1[C:25]([CH3:26])=[C:23]([CH3:24])[C:22]2[O:21][C:18]([CH3:20])([CH3:19])[CH2:17][CH2:16][C:15]=2[C:13]=1[CH3:14])(=[O:10])=[O:11]

Komponenten

Reaktionsbedingungen

Temperatur: 30 °C

Versuchsvorschrift

Fmoc-Arg(Pmc)-OH (0.5 g, 0.75 mmol) and Fmoc-Trp-OH (0.43 g, 0.1 mmol) was dissolved in 10 ml 100% TFA and heated at 30° C. for 1.5 hours. After evaporation of TFA, Fmoc-Arg-OH was removed by column chromatography on silica gel with heptane/ethyl acetate 2:1 as mobile phase. Fmoc-Trp(2Pmc)-OH was isolated by preparative HPLC (C18, 70-100% B in 15 min., tR 14.8 min, (A: H2O+0.1% TFA; B: CH3CN+0.1% TFA)). Isolated yield 130 mg (0.19 mmol, 25%).

Aufarbeitung

customAfter evaporation of TFA, Fmoc-Arg-OH
customwas removed by column chromatography on silica gel with heptane/ethyl acetate 2:1 as mobile phase

Quellen und Nachweise

ORD-Eintrag: ord-5084c9e428ae4f7c91bf3eea7361e819
Quelldatensatz: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patentnummer: US09109048B2

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