Acetic Acid → HCID 178510997, compound

HRID 1462856Notes

Reaction equation

HRID 1462856 reaction equation
[NH:1](C(OCC1C=CC=CC=1)=O)[CH2:2][C:3]([NH:5][C@H:6]([C:16]([NH:18][C@H:19]([C:26]([NH:28][C@H:29]([C:45]([O:47]CC1C=CC=CC=1)=[O:46])[CH2:30][CH2:31][CH2:32][CH2:33][NH:34]C(OCC1C=CC=CC=1)=O)=[O:27])[CH2:20][C:21]1[N:25]=[CH:24][NH:23][CH:22]=1)=[O:17])[CH2:7][O:8]CC1C=CC=CC=1)=[O:4].CO.C(O)(=O)C.O>[H][H].[Pd]>[NH2:1][CH2:2][C:3]([NH:5][C@H:6]([C:16]([NH:18][C@H:19]([C:26]([NH:28][C@H:29]([C:45]([OH:47])=[O:46])[CH2:30][CH2:31][CH2:32][CH2:33][NH2:34])=[O:27])[CH2:20][C:21]1[N:25]=[CH:24][NH:23][CH:22]=1)=[O:17])[CH2:7][OH:8])=[O:4]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 887MethanolHCID 962WaterHCID 178521357HCID 178521357, compound2×

Product 1

HCID 178510997HCID 178510997, compoundYield 70.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 178418361HCID 178418361, compoundSolvent

Procedure

10.5 g of palladium-on-charcoal was added to 23.2 g of Z-Gly-Ser(Bzl)-His-Lys(Z)-OBzl (Compound 11) suspended in a mixed solvent of 160 ml of methanol, 40 ml of acetic acid and 20 ml of water, and stirring was continued under atmospheric pressure in hydrogen atmosphere for 38 hours. After the catalyst was filtered off, the filtrate was washed with water and concentrated. The crude product was dissolved in water and eluted with 0.5N ammonia water using a strongly acidic ion exchange resin (NH4 +type). The eluate was concentrated and crystallized to obtain 8.0 g of Gly-Ser-His-Lys (Compound 20).

Workup

  1. customfor 38 hours
  2. filtrationAfter the catalyst was filtered off
  3. washthe filtrate was washed with water
  4. concentrationconcentrated
  5. dissolutionThe crude product was dissolved in water
  6. washeluted with 0.5N ammonia water using a strongly acidic ion exchange resin (NH4 +type)
  7. concentrationThe eluate was concentrated
  8. customcrystallized

Sources & evidence

ORD record
ord-92a3c5b52e624cc1ab1475bab7119120
Source dataset
uspto-grants-1984_07
Patent number
US04461724

Reaction notes

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