Tert-butyl (2S)-2-amino-3-[4-(tert-butoxy)phenyl]propanoate → Piperidine

HRID 1647122

Reaktionsgleichung

Reaktionsgleichung von HRID 1647122
[CH:1]1[C:13]2[CH:12]([O:14][C:15]([NH:17][C@H:18]([C:27](O)=[O:28])[CH2:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])=[O:16])[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:30]([O:34][C:35](=[O:50])[C@H:36]([CH2:38][C:39]1[CH:44]=[CH:43][C:42]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[CH:41][CH:40]=1)[NH2:37])([CH3:33])([CH3:32])[CH3:31]>>[C:30]([O:34][C:35](=[O:50])[C@H:36]([CH2:38][C:39]1[CH:44]=[CH:43][C:42]([O:45][C:46]([CH3:49])([CH3:48])[CH3:47])=[CH:41][CH:40]=1)[NH:37][C:27](=[O:28])[C@H:18]([CH2:19][C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[NH:17][C:15]([O:14][CH:12]1[C:13]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[C:6]2[C:11]1=[CH:10][CH:9]=[CH:8][CH:7]=2)=[O:16])([CH3:32])([CH3:33])[CH3:31].[NH:37]1[CH2:36][CH2:38][CH2:39][CH2:40][CH2:41]1

Komponenten

4

Edukt 2

HCID 7350495Tert-butyl (2S)-2-amino-3-[4-(tert-butoxy)phenyl]propanoateHCID 54139735N-[(9H-fluoren-9-yloxy)carbonyl]-3-(t-butoxycarbonyl)-L-alanine

Produkt 2

HCID 8082PiperidineHCID 22849520N-[N-[(9H-fluoren-9-yloxy)carbonyl]-3-(t-butoxycarbonyl)-L-alanyl]-3-(p-t-butoxyphenyl)-L-alanine t-butyl ester

Versuchsvorschrift

N-[(9H-fluoren-9-yloxy)carbonyl]-3-(t-butoxycarbonyl)-L-alanine and 3-(p-t-butoxyphenyl)-L-alanine t-butyl ester were coupled to give N-[N-[(9H-fluoren-9-yloxy)carbonyl] -3-(t-butoxycarbonyl)-L-alanyl]-3-(p-t-butoxyphenyl)-L-alanine t-butyl ester and 5 ml of piperidine and the reaction solution was evaporated. The residue was suspended in methanol and insoluble material was filtered off. The filtrate was evaporated and chromatographed on silica gel using ethyl acetate to yield 2 g of 3-(t-butoxyphenyl)-N-[3-(p-t-butoxy-carbonyl)-L-alanyl]-L-alanine t-butyl ester.

Quellen und Nachweise

ORD-Eintrag
ord-7f5bcbe068aa4c0da47b21ff0835966c
Quelldatensatz
uspto-grants-1995_07
Patentnummer
US05430024

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