HCID 178418361, compound → HCID 178472729, compound

HRID 866896Notes

Reaction equation

HRID 866896 reaction equation
[ClH:1].[CH2:2]([O:4][C:5](=[O:26])[CH2:6][N:7]([C:12](=[O:25])[C@H:13]([CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:24])[NH2:23])[NH:14][N+]([O-])=O)[CH2:8][CH2:9][O:10][CH3:11])[CH3:3].[H][H]>C(O)C.[Pd]>[ClH:1].[CH2:2]([O:4][C:5](=[O:26])[CH2:6][N:7]([C:12](=[O:25])[C@H:13]([CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:23])[NH2:24])[NH2:14])[CH2:8][CH2:9][O:10][CH3:11])[CH3:3]

Participants

5

Reactant 2

HCID 178418361HCID 178418361, compoundHCID 178472724HCID 178472724, compound

Product 1

HCID 178472729HCID 178472729, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of 4.0 g of NG -nitro-L-arginyl-N-(2-methoxyethyl)glycine ethyl ester hydrochloride in 50 ml of ethanol was added 0.5 g of palladium-black and then the mixture was shaken in a hydrogen atmosphere for 150 hours at room temperature. At the end of this period, the ethanol solution was filtered to remove the catalyst and evaporated to give an oily product. Reprecipitation with ethanol-ethyl ether gave 3.0 g (81%) of L-arginyl-N-(2-methoxyethyl)glycine ethyl ester hydrochloride in the form of a powder.

Workup

  1. filtrationAt the end of this period, the ethanol solution was filtered
  2. customto remove the catalyst
  3. customevaporated
  4. customto give an oily product
  5. customReprecipitation with ethanol-ethyl ether

Sources & evidence

ORD record
ord-4869934260b94613bc2e5cbe6ea26c88
Source dataset
uspto-grants-1978_07
Patent number
US04101653

Reaction notes

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