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

HRID 327526

Reaction equation

HRID 327526 reaction equation
[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

Participants

4

Reactant 2

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

Product 2

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

Procedure

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.

Sources & evidence

ORD record
ord-a8aadd92f54c4cd1a120c3378232101b
Source dataset
uspto-grants-1993_12
Patent number
US05273982

Linked notes

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