HCID 178516177, compound → HCID 178516178, compound

HRID 268457Notes

Reaction equation

HRID 268457 reaction equation
C([O:8][C:9](=[O:40])[C@H:10]([CH2:30][C:31]1[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[NH:33][CH:32]=1)[NH:11][C:12](=[O:29])[C@H:13]([CH2:23][C:24]1[N:28]=[CH:27][NH:26][CH:25]=1)[NH:14][C:15](=[O:22])[C@@H:16]1[CH2:20][CH2:19][C:18](=[O:21])[NH:17]1)C1C=CC=CC=1>[Pd].C(O)(=O)C>[O:21]=[C:18]1[NH:17][C@H:16]([C:15]([NH:14][C@H:13]([C:12]([NH:11][C@H:10]([C:9]([OH:40])=[O:8])[CH2:30][C:31]2[C:39]3[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=3)[NH:33][CH:32]=2)=[O:29])[CH2:23][C:24]2[N:28]=[CH:27][NH:26][CH:25]=2)=[O:22])[CH2:20][CH2:19]1

Participants

4

Reactant 1

HCID 178516177HCID 178516177, compound

Product 1

HCID 178516178HCID 178516178, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A mixture of N-[N-(5-oxo-L-prolyl)-L-histidyl]-L-tryptophan benzyl ester (Ex. 1, 0.300 g, 0.555 mmol) and 5 percent palladium on carbon (0.060 g) in glacial acetic acid (30 ml) is stirred rapidly under an atmosphere of hydrogen for 16 hours at room temperature. The mixture is filtered through diatomaceous earth ("Celite") and the filtrate is concentrated under reduced pressure. The residue is dissolved in methanol (10 ml) and diethyl ether (100 ml) is slowly added with vigorous stirring. The precipitate is collected, dissolved in methanol (10 ml) and diethyl ether (100 ml) is slowly added. The precipitate is collected, dissolved in methanol, treated with charcoal (0.20 g) and filtered through diatomaceous earth ("Celite"). The filtrate is evaporated to yield the title compound as a hard white glass which is used as such in a subsequent step.

Workup

  1. filtrationThe mixture is filtered through diatomaceous earth ("Celite")
  2. concentrationthe filtrate is concentrated under reduced pressure
  3. dissolutionThe residue is dissolved in methanol (10 ml)
  4. additiondiethyl ether (100 ml) is slowly added with vigorous stirring
  5. customThe precipitate is collected
  6. dissolutiondissolved in methanol (10 ml)
  7. additiondiethyl ether (100 ml) is slowly added
  8. customThe precipitate is collected
  9. dissolutiondissolved in methanol
  10. additiontreated with charcoal (0.20 g)
  11. filtrationfiltered through diatomaceous earth ("Celite")
  12. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-888d7e7934a241ac8175838b58dc9877
Source dataset
uspto-grants-1976_03
Patent number
US03947569

Reaction notes

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