Hydrochloric Acid → HCID 178512878, compound

HRID 1906136Notes

Reaction equation

HRID 1906136 reaction equation
[N:1]1(C(OC(C)(C)C)=O)[CH2:33][CH2:32][CH2:31][C@@H:2]1[C:3]([NH:5][C@H:6]([C:14]([NH:16][C@H:17]([C:28]([OH:30])=[O:29])[CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:27])[NH:23][N+]([O-])=O)=[O:15])[CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:4].O.Cl>Cl.CC(O)=O.CO.[Pd]>[NH:1]1[CH2:33][CH2:32][CH2:31][C@@H:2]1[C:3]([NH:5][C@H:6]([C:14]([NH:16][C@H:17]([C:28]([OH:30])=[O:29])[CH2:18][CH2:19][CH2:20][NH:21][C:22](=[NH:23])[NH2:27])=[O:15])[CH2:7][C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)=[O:4]

Participants

7

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 178451945HCID 178451945, compound

Product 1

HCID 178512878HCID 178512878, compoundYield 95.3%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 22641269Acetate-hydrochloric acidSolvent

Procedure

0.90 Gram (1.28 m mole) of BOC-D-Pro-Phe-Arg(NO2)-CHA was dissolved in 3.8 ml of 2N-HCl/AcOH with a small amount of MeOH and reacted at room temperature for 2 hours. After the reaction was completed, the solvent was removed by evaporation under reduced pressure, the residue thus obtained was suspended in 113 ml of MeOH, 37 ml of H2O and 2.2 ml of 1N-HCl. Next, 1 g of palladium black was added thereto and reduced by hydrogenation at 30° C. for 6 hours. After the hydrogenation was completed, the catalyst was removed by filtration and the solvent was also removed by evaporation under reduced pressure. The residue thus obtained was purified by using a gel filtration using TOYOPEARL HW 40F column with MeOH as the developing solvent to obtain 0.66 g (95.3%) of H-D-Pro-Phe-Arg-CHA.2HCl.

Workup

  1. customreacted at room temperature for 2 hours
  2. customthe solvent was removed by evaporation under reduced pressure
  3. customthe residue thus obtained
  4. customthe catalyst was removed by filtration
  5. customthe solvent was also removed by evaporation under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified
  8. filtrationa gel filtration

Sources & evidence

ORD record
ord-2a438607d2e144218ce39f94633189dc
Source dataset
uspto-grants-1987_03
Patent number
US04650753

Reaction notes

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