Hydrochloric Acid → HCID 178512861, compound

HRID 1197074Notes

Reaction equation

HRID 1197074 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]([N:9]1[CH2:30][CH2:29][CH2:28][C@H:10]1[C:11]([NH:13][C@H:14]([C:25]([OH:27])=[O:26])[CH2:15][CH2:16][CH2:17][NH:18][C:19](=[NH:24])[NH:20][N+]([O-])=O)=[O:12])=[O:8].CO.Cl>[Pd].O>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([N:9]1[CH2:30][CH2:29][CH2:28][C@H:10]1[C:11]([NH:13][C@H:14]([C:25]([OH:27])=[O:26])[CH2:15][CH2:16][CH2:17][NH:18][C:19](=[NH:20])[NH2:24])=[O:12])=[O:8]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 178512171Z-PyroGlu-Pro-Arg(NO2)

Product 1

HCID 178512861HCID 178512861, compoundYield 126.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

After 0.60 g (0.87 mmol) of Z-PyroGlu-Pro-Arg(NO2)-CHA was suspended in a solvent mixture of 112.5 ml of MeOH, 35.8 ml of H2O and 1.7 ml of 1N-HCl, 1 g of palladium black was added to the suspension followed by catalytic reduction at 30° C. for 5 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 0.42 g (87.5%) of H-PyroGlu-Pro-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-82075349c754483f80cedbdcea86ae76
Source dataset
uspto-grants-1992_05
Patent number
US05116941

Reaction notes

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