(R)-(((Phenylmethoxy)carbonyl)amino)phenylacetic acid → tert-butyl (2S)-2-[(Z)-N'-[(2R)-2-phenyl-2-(phenylmethoxycarbonylamino)acetyl]oxycarbamimidoyl]piperidine-1-carboxylate

HRID 397702Notes

Reaction equation

HRID 397702 reaction equation
[NH2:1]/[C:2](=[N:16]\[OH:17])/[C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10].[CH2:18]([O:25][C:26]([NH:28][C@H:29]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[C:30](O)=[O:31])=[O:27])[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>>[NH2:1]/[C:2](/[C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1[C:9]([O:11][C:12]([CH3:14])([CH3:13])[CH3:15])=[O:10])=[N:16]\[O:17][C:30](=[O:31])[C@@H:29]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)[NH:28][C:26](=[O:27])[O:25][CH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

3

Reactant 2

HCID 87183(R)-(((Phenylmethoxy)carbonyl)amino)phenylacetic acidHCID 59085902tert-butyl (2S)-2-[(Z)-N'-hydroxycarbamimidoyl]piperidine-1-carboxylate

Product 1

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

Procedure

The title compound was prepared by a similar method to Preparation 5 from tert-butyl (Z)-(2S)-2-[amino(hydroxyimino)methyl]-1-piperidinecarboxylate [see Preparation 4] and (2R)-2-{[(benzyloxy)carbonyl]amino}-2-phenylethanoic acid to afford 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 as an oil.

Sources & evidence

ORD record
ord-04558f21ea454df683733f3658afb003
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

Loading…