HCID 86755835, compound → HCID 131716382, compound

HRID 1650900Notes

Reaction equation

HRID 1650900 reaction equation
[N:1]#[N:2].[CH2:3]([O:5][C:6]([CH:8]([NH:18][C@H:19]([C:31]([OH:33])=[O:32])[CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:30])[C:26]([F:29])([F:28])[F:27])[CH2:9][C:10](=O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])[CH3:4].N#N.C(C(N[C@H](C(O)=O)CCCCN)CCC1C=CC=CC=1)(O)=O>[Ni].[Pd]>[N:1]#[N:2].[CH2:3]([O:5][C:6]([CH:8]([NH:18][C@H:19]([C:31]([OH:33])=[O:32])[CH2:20][CH2:21][CH2:22][CH2:23][NH:24][C:25](=[O:30])[C:26]([F:27])([F:28])[F:29])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=[O:7])[CH3:4]

Participants

5

Reactant 2

HCID 86755835HCID 86755835, compoundHCID 131716383HCID 131716383, compound

Product 1

HCID 131716382HCID 131716382, compound

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 23938PalladiumCatalyst2×

Procedure

The N2 -(1-carboxy-3-oxo-3-phenylpropyl)-L-lysine derivative can be subjected to catalytic hydrogenolysis proceeding gently in water, an alcohol or a polar protic solvent such as acetic acid in the presence of a suitable amount of an acid such as sulfuric acid, hydrochloric acid or formic acid to give the N2 -(1-carboxy-3-phenylpropyl)-L-lysine derivative in a high yield. In catalytic hydrogenolysis, palladium, Raney nickel, and the like are examples of suitable catalysts. For instance, when N2 -[1-ethoxycarbonyl-3-oxo-3-phenylpropyl]-N6 -trifluoroacetyl-L-lysine is subjected to catalytic hydrogenolysis, the lysine derivative is hydrogenated in an alcohol (such as ethanol) as the solvent in the presence of the acid at a temperature of 0° C. to 60° C., preferably from 5° C. to 40° C. for several to 24 hours by using palladium/carbon as the catalyst to give almost quantitatively N2 -(1-ethoxycarbonyl-3-phenylpropyl)-N6 -trifluoroacetyl-L-lysine. After completing the hydrogenation, the catalyst is removed from the reaction mixture, the acid of the resulting solution is neutralized with an alkali, from which the solvent is distilled away, and then the desired compound having the (S,S)-configuration can be isolated in a usual manner such as extraction. If necessary, recrystallization can be conducted from the obtained reaction mixture.

Workup

  1. customseveral to 24 hours

Sources & evidence

ORD record
ord-1bf7af0fb9934a2694c2a3ff89ea7373
Source dataset
uspto-grants-1990_05
Patent number
US04925969

Reaction notes

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