6-[5-(1-Benzyloxycarbonyl-1-methyl-ethyl)-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester → 6-[5-(1-carboxy-1-methyl-ethyl)-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester

HRID 712716Notes

Reaction equation

HRID 712716 reaction equation
[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:19]=[N:20][CH:21]=[C:22]([C:24]([C:27]([O:29]CC4C=CC=CC=4)=[O:28])([CH3:26])[CH3:25])[CH:23]=3)=[CH:15][N:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6]([N:8]1[C:17]2[C:12](=[CH:13][C:14]([C:18]3[CH:19]=[N:20][CH:21]=[C:22]([C:24]([C:27]([OH:29])=[O:28])([CH3:26])[CH3:25])[CH:23]=3)=[CH:15][N:16]=2)[CH2:11][CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 1

HCID 1176673576-[5-(1-Benzyloxycarbonyl-1-methyl-ethyl)-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester

Product 1

HCID 1176677586-[5-(1-carboxy-1-methyl-ethyl)-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl esterYield 40.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

To a stirred solution of 6-[5-(1-benzyloxycarbonyl-1-methyl-ethyl)-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester (500 mg, 1.0 mmol) in MeOH (25 mL) is added 10% Pd/C (250 mg). The reaction mixture is stirred under 40 psi H2 for 16 h. The catalyst is removed by filtration through diatomaceous earth and the solvent is evaporated to afford 160 mg of 6-[5-(1-carboxy-1-methyl-ethyl)-pyridin-3-yl]-3,4-dihydro-2H-[1,8]naphthyridine-1-carboxylic acid tert-butyl ester

Workup

  1. customThe catalyst is removed by filtration through diatomaceous earth
  2. customthe solvent is evaporated

Sources & evidence

ORD record
ord-d5d6103ed58e4822afbaa0c0c26a4a0e
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

Loading…