Hydrochloric Acid → HCID 70566171, compound

HRID 1155076Notes

Reaction equation

HRID 1155076 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:7]([N:9]1[CH2:16][CH2:15][CH2:14][C@H:10]1[C:11]([NH2:13])=[O:12])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].[ClH:27]>CO.[Pd]>[NH2:1][C@H:2]([C:7]([N:9]1[CH2:16][CH2:15][CH2:14][C@H:10]1[C:11]([NH2:13])=[O:12])=[O:8])[C@H:3]([CH2:5][CH3:6])[CH3:4].[ClH:27]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 54172261HCID 54172261, compound

Product 1

HCID 70566171HCID 70566171, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×

Procedure

24.0 g (66.5 mmoles) of Z-Ile-Pro-NH2 are dissolved in 470 ml of methanol, and 30 ml of a 2.4 n hydrochloric acid solution in methanol and 4 g of a 10% palladium-on-carbon catalyst are added to the solution. Hydrogen is bubbled through the mixture for one hour, thereafter the catalyst is filtered off and the filtrate is evaporated. The residue is triturated with ether, and the resulting 20 g of crude product is recrystallized from a mixture of methanol and ether. 16.05 g (81%) of H-Ile-Pro-NH2.HCl are obtained; m.p.: 135°-140° C., Rf4 =0.15.

Workup

  1. customHydrogen is bubbled through the mixture for one hour
  2. filtrationthe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. customThe residue is triturated with ether
  5. customthe resulting 20 g of crude product is recrystallized from a mixture of methanol and ether

Sources & evidence

ORD record
ord-57d447a03e11497ca8a8139335654dae
Source dataset
uspto-grants-1981_11
Patent number
US04299821

Reaction notes

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