Oxalic acid dihydrate → HCID 9856408, compound

HRID 1155085Notes

Reaction equation

HRID 1155085 reaction equation
[N:1]1(C(OCC2C=CC=CC=2)=O)[CH2:18][CH2:17][CH2:16][C@H:2]1[C:3]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:4].O.O.C(O)(=O)C(O)=O>CO.[Pd]>[NH:1]1[CH2:18][CH2:17][CH2:16][C@H:2]1[C:3]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH3:15])=[O:4]

Participants

5

Reactant 2

HCID 61373Oxalic acid dihydrateHCID 53926994HCID 53926994, compound

Product 1

HCID 9856408HCID 9856408, compoundYield 118.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

5.0 g (12.9 mmoles) of Z-Pro-NH-C10H21 and 2.02 g (16 mmoles) of oxalic acid dihydrate are dissolved in 100 ml of methanol, 0.8 g of a 10% palladium-on-carbon catalyst are added, and hydrogen is bubbled through the mixture for 2 hours. The reaction mixture is heated, the catalyst is filtered off, and the filtrate is evaporated. The crystalline residue is triturated with ether and then filtered off to obtain 3.9 g (88%) of H-Pro-NH-C10H21.(COOH)2 ; m.p.: 152°-154° C., Rf3 =0.16.

Workup

  1. customhydrogen is bubbled through the mixture for 2 hours
  2. temperatureThe reaction mixture is heated
  3. filtrationthe catalyst is filtered off
  4. customthe filtrate is evaporated
  5. customThe crystalline residue is triturated with ether
  6. filtrationfiltered off

Sources & evidence

ORD record
ord-0c506ea1a68d4a8cbeb7f81ba66418a6
Source dataset
uspto-grants-1981_11
Patent number
US04299821

Reaction notes

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