Ethanol → 2-[(2-Quinolinylcarbonyl)amino]butanediamide

HRID 53655Notes

Reaction equation

HRID 53655 reaction equation
C1(CNC([NH:11][CH:12]([CH2:16][C:17]([NH2:19])=[O:18])[C:13]([NH2:15])=[O:14])=O)C=CC=CC=1.C(O)C.[N:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[C:33]([O-:35])=O>[Pd].ClCCl>[N:23]1[C:32]2[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH:26]=[CH:25][C:24]=1[C:33]([NH:11][CH:12]([CH2:16][C:17]([NH2:19])=[O:18])[C:13]([NH2:15])=[O:14])=[O:35]

Participants

6

Reactant 3

HCID 702EthanolHCID 3538644QuinaldateHCID 216107972-[(Phenylmethylcarbamoyl)amino]butanediamide

Product 1

HCID 218311332-[(2-Quinolinylcarbonyl)amino]butanediamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6344DichloromethaneSolvent

Procedure

A solution of [1S-[1R*(R*),2S*]]-N1[3-[[[(1,1-dimethylethyl)amino]carbonyl]n-butyl)amino]-2-hydroxy-1-(phenylmethy)propyl]-2-[(phenylmethylcarbamoyl)amino]-butanediamide (1.03 g, 1.77 mmol) in 40 mL of abs. ethanol is then deprotected by hydrogenolysis in the presence of 10% palladium on carbon catalyst to give, after filtration and concentration, the free amine (428 mg) which was coupled with N-hydroxysuccinimide ester of 2-quinoline carboxylate (270 mg, 1.0 mmol) in dichloromethane for 16 h to give 380 mg, 63% of [1S-[1R*(R*),2S*]]-N1[3-[[[1,1-dimethylethyl)amino]carbonyl](n-butyl)amino]-2-hydroxy-1-(phenylmethyl)propyl]-2-[(2-quinolinylcarbonyl)amino]-butanediamide, mp 102.1°-103° C.

Workup

  1. customto give
  2. filtrationafter filtration and concentration

Sources & evidence

ORD record
ord-75e4cef93a7d4fea84f74889145c8929
Source dataset
uspto-grants-1997_04
Patent number
US05620977

Reaction notes

Loading…