Hydrochloric Acid → HCID 178462135, compound

HRID 1197072Notes

Reaction equation

HRID 1197072 reaction equation
[N:1]1(C(OCC2C=CC=CC=2)=O)[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:9][C@H:10]([C:12]([NH:14][C@H:15]([C:26]([OH:28])=[O:27])[CH2:16][CH2:17][CH2:18][NH:19][C:20](=[NH:25])[NH:21][N+]([O-])=O)=[O:13])[CH3:11])=[O:8].CO.Cl>[Pd].O>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:9][C@H:10]([C:12]([NH:14][C@H:15]([C:26]([OH:28])=[O:27])[CH2:16][CH2:17][CH2:18][NH:19][C:20](=[NH:21])[NH2:25])=[O:13])[CH3:11])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 178462136HCID 178462136, compound

Product 1

HCID 178462135HCID 178462135, compoundYield 50.8%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

After 1.75 g (2.6 mmols) of Z-PyroGlu-Ala-Arg(NO2)-CHA was suspended in a solvent mixture of 112.5 ml of MeOH, 27.7 ml of H2O and 9.8 ml of 1N-HCl, 1 g of palladium black was added to the suspension followed by catalytic reduction at 30° C. for 6 hours. After the reaction, the catalyst was filtered off and the solvent was removed by distillation under reduced pressure. The residue was purified through TOYOPEARL HW40F column using MeOH as a developing solvent to give 0.471 g (34.4%) of H-PyroGlu-Ala-Arg-CHA.HCl.

Workup

  1. additionwas added to the suspension
  2. customAfter the reaction
  3. filtrationthe catalyst was filtered off
  4. customthe solvent was removed by distillation under reduced pressure
  5. customThe residue was purified through TOYOPEARL HW40F column

Sources & evidence

ORD record
ord-aeaa3c673fd643ca9ee65199d01496ef
Source dataset
uspto-grants-1992_05
Patent number
US05116941

Reaction notes

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