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

반응식

[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

참가 물질

반응물 2

HCID 7350495Tert-butyl (2S)-2-amino-3-[4-(tert-butoxy)phenyl]propanoate

HCID 54139735N-[(9H-fluoren-9-yloxy)carbonyl]-3-(t-butoxycarbonyl)-L-alanine

생성물 2

HCID 8082Piperidine

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

실험 절차

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.