Hydrochloric Acid → HCID 178462176, compound

HRID 1906138Notes

Reaction equation

HRID 1906138 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@@H:2]([C:4]([NH:6][C@H:7]([C:15]([NH:17][C@H:18]([C:29]([OH:31])=[O:30])[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[NH:28])[NH:24][N+]([O-])=O)=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:3].CO.Cl>[Pd].O>[NH2:1][C@@H:2]([C:4]([NH:6][C@H:7]([C:15]([NH:17][C@H:18]([C:29]([OH:31])=[O:30])[CH2:19][CH2:20][CH2:21][NH:22][C:23](=[NH:24])[NH2:28])=[O:16])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:5])[CH3:3]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 178462189HCID 178462189, compound

Product 1

HCID 178462176HCID 178462176, compoundYield 78.2%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 962WaterSolvent

Procedure

2.3 Grams (3.25 m moles) of Z-D-Ala-Phe-Arg(NO2)-CHA was suspended in a mixed solvent of 113 ml of MeOH, 35 ml of H2O and 2.1 ml of 1N-HCl. To this suspension was added 1 g of palladium black and reduced by hydrogenation at 30° C. for 4 hours. After the hydrogenation was completed the catalyst was removed by filtration, further the solvent was removed by evaporation under reduced pressure. The residue thus obtained was purified by using a gel filtration column of TOYOPEARL HW 40F with MeOH as the developing solvent to obtain 1.5 g (78.2%) of H-D-Ala-Phe-Arg-CHA.2HCl.

Workup

  1. customwas removed by filtration
  2. customfurther the solvent was removed by evaporation under reduced pressure
  3. customThe residue thus obtained
  4. customwas purified
  5. filtrationa gel filtration column of TOYOPEARL HW 40F with MeOH as the developing solvent

Sources & evidence

ORD record
ord-a3a890be83054b86a6a0757630283d7e
Source dataset
uspto-grants-1987_03
Patent number
US04650753

Reaction notes

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