HCID 178513426, compound → tert-butyl (2S)-2-{5-[(1-[(benzyloxy)carbonyl]-4-piperidyloxy)methyl]-1,2,4-oxadiazol-3-yl}-1-piperidinecarboxylate

HRID 397697Notes

Reaction equation

HRID 397697 reaction equation
[NH2:1]/[C:2](=[N:12]\[O:13][C:14](=O)[CH2:15][O:16][CH:17]1[CH2:22][CH2:21][N:20]([C:23]([O:25][CH2:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:24])[CH2:19][CH2:18]1)/[C@@H:3]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]1[C:9]([O-:11])=[O:10]>N1C=CC=CC=1>[CH2:26]([O:25][C:23]([N:20]1[CH2:21][CH2:22][CH:17]([O:16][CH2:15][C:14]2[O:13][N:12]=[C:2]([C@@H:3]3[CH2:8][CH2:7][CH2:6][CH2:5][N:4]3[C:9]([O:11][C:27]([CH3:32])([CH3:28])[CH3:26])=[O:10])[N:1]=2)[CH2:18][CH2:19]1)=[O:24])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

3

Reactant 1

HCID 178513426HCID 178513426, compound

Product 1

HCID 57120376tert-butyl (2S)-2-{5-[(1-[(benzyloxy)carbonyl]-4-piperidyloxy)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 13 from (Z)-(2S)-2-[amino([2-(1-[(benzyloxy)carbonyl]-4-piperidyloxy)acetyl]oxyimino)methyl]-1-piperidinecarboxylate [see Preparation 93] and pyridine. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 80:20, changing to 50:50, by volume, hexane:ethyl acetate, in 5% increments, to afford tert-butyl (2S)-2-{5-[(1-[(benzyloxy)carbonyl]-4-piperidyloxy)methyl]-1,2,4-oxadiazol-3-yl}-1-piperidinecarboxylate.

Workup

  1. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 80:20

Sources & evidence

ORD record
ord-ed9d702eca9c435b9f7a27340bf36246
Source dataset
uspto-grants-2003_08
Patent number
US06610707B1

Reaction notes

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