Hydrochloric Acid → HCID 178419603, compound

HRID 1076420Notes

Reaction equation

HRID 1076420 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[C@H:2]([C:10]([NH:12][C@H:13]([C:21]([NH:23][C@H:24]([C:31]([NH:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[O:32])[CH2:25][O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:22])[CH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:9])[NH2:8].[BrH:49].[ClH:50].O1CCOCC1>CO.[Pd]>[NH2:1][C@H:2]([C:10]([NH:12][C@H:13]([C:21]([NH:23][C@H:24]([C:31]([NH:33][CH2:34][C:35]([O:37][CH3:38])=[O:36])=[O:32])[CH2:25][O:26][C:27]([CH3:30])([CH3:29])[CH3:28])=[O:22])[CH2:14][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=1)=[O:11])[CH2:3][CH2:4][CH2:5][NH:6][C:7](=[NH:8])[NH2:9].[ClH:50].[BrH:49]

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 178419602HCID 178419602, compound

Product 1

HCID 178419603HCID 178419603, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

6.3 g of Z-Arg-Phe-Ser(tBu)-Gly-OCH3 hydrobromide (8.5 mmols) are dissolved in 350 ml of methanol and 2.9 ml of hydrogen chloride in dioxane (3.09 N, 8.9 mmols) are added. The mixture is hydrogenated in the presence of 1.2 g of 10 % strength palladium-charcoal at room temperature and atmospheric pressure. After completion of the hydrogen uptake the solution is filtered and evaporated and the resulting residue is dissolved in 30 ml of methanol and the solution stirred into 700 ml of ether. Thereby a yellowish paste is produced which is again dissolved and precipitated in the same manner.

Workup

  1. filtrationAfter completion of the hydrogen uptake the solution is filtered
  2. customevaporated
  3. dissolutionthe resulting residue is dissolved in 30 ml of methanol
  4. customThereby a yellowish paste is produced which
  5. dissolutionis again dissolved
  6. customprecipitated in the same manner

Sources & evidence

ORD record
ord-cc5d929b73634febb4ed406368ac588c
Source dataset
uspto-grants-1976_05
Patent number
US03956260

Reaction notes

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