Reaction #72084

ord-f3fb8dc7ab42419ca6ac2a4644558142

Reaction equation

COC(=O)c1cc(N2CC[C@H](NC(=O)OCc3ccccc3)[C@H](OC)C2)ccc1NC(C)=O
Methyl cis(±)-2-(acetylamino)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)benzoate
[H][H]
hydrogen
→
COC(=O)c1cc(N2CC[C@H](N)[C@H](OC)C2)ccc1NC(C)=O
title compound
COC(=O)c1cc(N2CC[C@H](N)[C@H](OC)C2)ccc1NC(C)=O
Methyl cis(±)-2-(acetylamino)-5-(4-amino-3-methoxypiperidin-1-yl)benzoate

Reactants

COC(=O)c1cc(N2CC[C@H](NC(=O)OCc3ccccc3)[C@H](OC)C2)ccc1NC(C)=O
Methyl cis(±)-2-(acetylamino)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)benzoate
[H][H]
hydrogen

Reagents

[C].[Pd]
palladium-carbon

Solvents

CCO
ethanol

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    FiltrationThe reaction solution was filtered through celite
  2. 2
    Concentrationconcentrated under reduced pressure

Procedure

Methyl cis(±)-2-(acetylamino)-5-(4-{[(benzyloxy)carbonyl]amino}-3-methoxypiperidin-1-yl)benzoate obtained in Example (185c) was dissolved in ethanol (25 mL). A 10% palladium-carbon catalyst (180 mg) was added, and the mixture was stirred in a hydrogen atmosphere overnight. The reaction solution was filtered through celite and then concentrated under reduced pressure to obtain 210 mg of the title compound. The resulting compound was used for the next reaction without purification.

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08536197B2uspto-grants-2013_09