Benzylamine → Cbz-Trp-NHBn

HRID 129716

Reaktionsgleichung

Reaktionsgleichung von HRID 129716
N(C(OCC1C=CC=CC=1)=O)[C@H](C(N[C@H](C(N)=O)C)=O)CC1C=CC=CC=1.[NH:28]([C:43]([O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:44])[C@H:29]([C:40]([OH:42])=O)[CH2:30][C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1.[CH2:53]([NH2:60])[C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1>C1COCC1>[NH:28]([C:43]([O:45][CH2:46][C:47]1[CH:52]=[CH:51][CH:50]=[CH:49][CH:48]=1)=[O:44])[C@H:29]([C:40]([NH:60][CH2:53][C:54]1[CH:59]=[CH:58][CH:57]=[CH:56][CH:55]=1)=[O:42])[CH2:30][C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1

Komponenten

5

Edukt 3

HCID 7504BenzylamineHCID 101176benzyloxycarbonyl-L-tryptophanHCID 7020268Z-Phe-ala-NH2

Produkt 1

HCID 16735215Cbz-Trp-NHBnAusbeute 89 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The coupling procedure described above for the preparation of Cbz-Phe-Ala-NH2 was employed using 10.0 g of Cbz-Trp-OH (Sigma Chemical Company) and 4.84 mL of freshly distilled BnNH2 in dry THF to give 11.3 g (89% yield) of crystalline Cbz-Trp-NHBn. Characteristic analytical data are as follows: mp 104°-105° C.; 1H NMR (300 MHz, CDCl3) δ8.00-6.88 (m, 16H, Ar), 5.85 (br, 1H, H-α), 5.45 (br, 1H, H-N), 5.10 (s, 2H, CH2--O), 4.57-4.45 (br, H-), 4.27 (t, 6H, CH2 --N), 3.38 (dd, J=4, 14 Hz, 1H, H-β), 3.16 (dd, J=8, 14 Hz, 1H, H-β); mass spectrum (EI), m/e 427 (M+), 336 (M+ -Bn), 277 (M+ -Cbz-NH), 130 (M+ -Cbz-NH-CH-CONH-Bn), 91 (Bn+); [α]25D +7.0° (c=0.20, EtOAC).

Quellen und Nachweise

ORD-Eintrag
ord-0cbcbc12ab1443dbb10d97fbc8be4ca6
Quelldatensatz
uspto-grants-1995_11
Patentnummer
US05470834

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