Z-Pro-Gly-NH2 → Prolylglycinamide

HRID 65601Notes

Reaction equation

HRID 65601 reaction equation
C(OC([N:11]1[CH2:22][CH2:21][CH2:20][C@H:12]1[C:13]([NH:15][CH2:16][C:17]([NH2:19])=[O:18])=[O:14])=O)C1C=CC=CC=1.[H][H]>[Pd].CO>[NH:11]1[CH2:22][CH2:21][CH2:20][C@H:12]1[C:13]([NH:15][CH2:16][C:17]([NH2:19])=[O:18])=[O:14]

Participants

5

Reactant 2

HCID 11902990Z-Pro-Gly-NH2HCID 178418361HCID 178418361, compound

Product 1

HCID 3013627Prolylglycinamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A mixture consisting of 33.5 g. of N-benzyloxycarbonyl-L-prolylglycinamide (this compound has been reported in Synthetic Peptides, Vol. 1, G. R. Pettit, Van Nostrand Reinhold Company, New York, 1970, page 151), 1 g. of 20% palladium-on-carbon, and 500 ml. of methanol is hydrogenated at 50 lbs./in.2 hydrogen pressure and room temperature for one hour. The mixture is filtered to remove the catalyst, and the filtrate is evaporated to dryness to give a solid residue of L-prolylglycinamide; m.p. 124°-127° C., following crystallization from acetonitrile-toluene; [α]D25 -48.5° (2% in water).

Workup

  1. filtrationThe mixture is filtered
  2. customto remove the catalyst
  3. customthe filtrate is evaporated to dryness

Sources & evidence

ORD record
ord-c16e6679b61c4397bb0c2a5e4df3b26a
Source dataset
uspto-grants-1978_12
Patent number
US04128540

Reaction notes

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