4-{2-[(4-Benzyloxycarbonylmethoxy-7-methyl-quinoline-2-carbonyl)-amino]-acetyl}-piperazine-1-carboxylic acid butyl ester → 4-{2-[(4-Carboxymethoxy-7-methyl-quinoline-2-carbonyl)-amino]-acetyl}-piperazine-1-carboxylic acid butyl ester

HRID 1185491Notes

Reaction equation

HRID 1185491 reaction equation
[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:42])[CH2:15][NH:16][C:17]([C:19]2[CH:28]=[C:27]([O:29][CH2:30][C:31]([O:33]CC3C=CC=CC=3)=[O:32])[C:26]3[C:21](=[CH:22][C:23]([CH3:41])=[CH:24][CH:25]=3)[N:20]=2)=[O:18])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4]>C(O)C.CN(C=O)C>[CH2:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([C:14](=[O:42])[CH2:15][NH:16][C:17]([C:19]2[CH:28]=[C:27]([O:29][CH2:30][C:31]([OH:33])=[O:32])[C:26]3[C:21](=[CH:22][C:23]([CH3:41])=[CH:24][CH:25]=3)[N:20]=2)=[O:18])[CH2:10][CH2:9]1)=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 1

HCID 685999324-{2-[(4-Benzyloxycarbonylmethoxy-7-methyl-quinoline-2-carbonyl)-amino]-acetyl}-piperazine-1-carboxylic acid butyl ester

Product 1

HCID 686005014-{2-[(4-Carboxymethoxy-7-methyl-quinoline-2-carbonyl)-amino]-acetyl}-piperazine-1-carboxylic acid butyl ester

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 5 g 4-{2-[(4-Benzyloxycarbonylmethoxy-7-methyl-quinoline-2-carbonyl)-amino]-acetyl}-piperazine-1-carboxylic acid butyl ester in 50 ml ethanol and 150 ml DMF were added under argon 732 mg Pd/C (10%) and the suspension was stirred under an atmosphere of hydrogen (5 bar) for 4 h. The suspension was filtered over a plug of Celite® and washed with ethanol and DMF. The crude product was obtained after evaporation of the solvent. Yield: 4.1 g.

Workup

  1. filtrationThe suspension was filtered over a plug of Celite®
  2. washwashed with ethanol and DMF

Sources & evidence

ORD record
ord-d28ac240f5ba494599d503961e80da6e
Source dataset
uspto-grants-2014_03
Patent number
US08669266B2

Reaction notes

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