Oxalic acid dihydrate → HCID 131717182, compound

HRID 2371372Notes

Reaction equation

HRID 2371372 reaction equation
[N:1](C(OCC1C=CC=CC=1)=O)([CH2:3][C:4]([NH:6][C@H:7]([C:16]([NH:18][C@H:19]([C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH:20]([CH3:22])[CH3:21])=[O:17])[CH2:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:5])[CH3:2].O.O.C(O)(=O)C(O)=O>CO.[Pd]>[NH:1]([CH2:3][C:4]([NH:6][C@H:7]([C:16]([NH:18][C@H:19]([C:23]([O:25][C:26]([CH3:27])([CH3:28])[CH3:29])=[O:24])[CH:20]([CH3:22])[CH3:21])=[O:17])[CH2:8][C:9](=[O:15])[O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 61373Oxalic acid dihydrateHCID 131717183HCID 131717183, compound

Product 1

HCID 131717182HCID 131717182, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

The oily Z-Sar-Asp(OtBu)-Val-OtBu protected tripeptide obtained in a yield of 4.2 g (7.6 mmol) (Rf1 =0.75) is dissolved in 40 ml of methanol and, after adding 0.8 g of palladium-on-carbon catalyst, the mixture is hydrogenated in the usual manner. After filtering off the catalyst, 1.0 g (8.0 mmol) of oxalic acid dihydrate is added to the filtrate, the solution is evaporated and the residue is solidified by adding ether to obtain 2.24 g of H-Sar-Asp(OtBu)-Val-OtBu.oxalate (free tripeptide oxalate), m.p.: 190°-192° C., Rf3 =0.30.

Workup

  1. customobtained in a yield of 4.2 g (7.6 mmol) (Rf1 =0.75)
  2. additionis added to the filtrate
  3. customthe solution is evaporated
  4. additionby adding ether

Sources & evidence

ORD record
ord-a68ad068fe6e49ac9189ffa702aded4b
Source dataset
uspto-grants-1992_03
Patent number
US05093320

Reaction notes

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