Oxalic Acid → HCID 87877562, compound

HRID 1357460Notes

Reaction equation

HRID 1357460 reaction equation
C(OC([NH:11][C@H:12]([C:16]([NH:18][C@H:19]([C:21]([O:23][CH3:24])=[O:22])[CH3:20])=[O:17])[CH:13]([CH3:15])[CH3:14])=O)C1C=CC=CC=1.[C:25]([OH:30])(=[O:29])[C:26]([OH:28])=[O:27]>CO.[Pd]>[C:25]([OH:30])(=[O:29])[C:26]([OH:28])=[O:27].[NH2:11][C@H:12]([C:16]([NH:18][C@H:19]([C:21]([O:23][CH3:24])=[O:22])[CH3:20])=[O:17])[CH:13]([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 971Oxalic AcidHCID 7015715Z-Val-ala-ome

Product 1

HCID 87877562HCID 87877562, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.69 g (8.0 mmol) of methyl benzyloxycarbonyl-L-valyl-L-alaninate [E. Klieger and E. Schr{overscore (o)}der: Ann. Chem. 661, 193 (1963)] are dissolved in 25 ml of methanol, 0.72 9 (8.0 mmol) of anhydrous oxalic acid and 0.1 g of Pd/C catalyst are added, then the mixture is submitted to hydrogenation at about 20° C. The catalyst is filtered off and the filtrate is evaporated at a pressure of 2.0-2.5 kPa. The crystalline residue is rubbed with diethyl ether, filtered, washed with diethyl ether and dried in a vacuum desiccator.

Workup

  1. customis submitted to hydrogenation at about 20° C
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated at a pressure of 2.0-2.5 kPa
  4. filtrationfiltered
  5. washwashed with diethyl ether
  6. customdried in a vacuum desiccator

Sources & evidence

ORD record
ord-4f53c5a3c08d42239086c78be94f88c5
Source dataset
uspto-grants-2003_07
Patent number
US06593300B1

Reaction notes

Loading…