Fmoc-L-tryptophan → N-(Fmoc-L-tryptophanyl)-1-amino-3-methylbutane

HRID 742991

Reaktionsgleichung

Reaktionsgleichung von HRID 742991
[NH:1]([C:16]([O:18][CH2:19][CH:20]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]2[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17])[C@H:2]([C:13](O)=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1>NCCC(C)C>[C:16]([NH:1][C@H:2]([C:13]([NH:1][CH2:2][CH2:3][CH:4]([CH3:12])[CH3:5])=[O:14])[CH2:3][C:4]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][CH:5]=1)([O:18][CH2:19][CH:20]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[C:26]2[C:21]1=[CH:22][CH:23]=[CH:24][CH:25]=2)=[O:17]

Komponenten

3

Edukt 1

HCID 978343Fmoc-L-tryptophan

Produkt 1

HCID 22865445N-(Fmoc-L-tryptophanyl)-1-amino-3-methylbutaneAusbeute 196,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 7894IsoamylamineLösungsmittel

Versuchsvorschrift

In substantially the same manner as in Example 5, 1-amino-3-methylbutane (405 μl) was condensed with Fmoc-Trp-OH (1.35 g, Peptide Institute, Inc.) to give N-(Fmoc-L-tryptophanyl)-1-amino-3-methylbutane (1.54 g) as a white powder (yield 98%). A portion (1.44 g) of this product was, in substantially the same manner as in Example 17, subjected to deprotection of Fmoc group, which was then condensed with (2S,3S)-ethyl hydrogen transepoxysuccinate as obtained in Reference Example 8 (432 mg) to yield the title compound (compound 88; 734 mg) as a white powder (yield 72%).

Quellen und Nachweise

ORD-Eintrag
ord-0e88a5bef1f54ec596166234daa51ec2
Quelldatensatz
uspto-grants-1996_09
Patentnummer
US05556853

Verknüpfte Notizen

Wird geladen…