tert-butyl (2S)-2-[(Z)-N'-[(2R)-2-phenyl-2-(phenylmethoxycarbonylamino)acetyl]oxycarbamimidoyl]piperidine-1-carboxylate → tert-butyl (2S)-2-{5-[(R)-{[(benzyloxy)carbonyl]amino}(phenyl)methyl]-1,2,4-oxadiazol-3-yl}-1-piperidinecarboxylate

HRID 397703Notes

Reaction equation

HRID 397703 reaction equation
[NH2:1]/[C:2](/[C@@H:25]1[CH2:30][CH2:29][CH2:28][CH2:27][N:26]1[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])=[N:3]\[O:4][C:5](=O)[C@@H:6]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[NH:7][C:8](=[O:17])[O:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>N1C=CC=CC=1>[CH2:10]([O:9][C:8]([NH:7][C@H:6]([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:5]1[O:4][N:3]=[C:2]([C@@H:25]2[CH2:30][CH2:29][CH2:28][CH2:27][N:26]2[C:31]([O:33][C:34]([CH3:37])([CH3:36])[CH3:35])=[O:32])[N:1]=1)=[O:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

3

Reactant 1

HCID 59085900tert-butyl (2S)-2-[(Z)-N'-[(2R)-2-phenyl-2-(phenylmethoxycarbonylamino)acetyl]oxycarbamimidoyl]piperidine-1-carboxylate

Product 1

HCID 57119964tert-butyl (2S)-2-{5-[(R)-{[(benzyloxy)carbonyl]amino}(phenyl)methyl]-1,2,4-oxadiazol-3-yl}-1-piperidinecarboxylate

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The title compound was prepared by a similar method to Preparation 6 from tert-butyl (2S)-2-[(Z,5R)-1-amino-4,7-dioxo-5,9-diphenyl-3,8-dioxa-2,6-diaza-1-nonen-1-yl]-1-piperidinecarboxylate [see Preparation 10 1] and pyridine to afford tert-butyl (2S)-2-{5-[(R)-{[(benzyloxy)carbonyl]amino}(phenyl)methyl]-1,2,4-oxadiazol-3-yl}-1-piperidinecarboxylate as an oil.

Sources & evidence

ORD record
ord-1d6f39fc62df461b97e6a19abf767629
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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