HCID 178513896, compound → HCID 178513940, compound

HRID 1155089Notes

Reaction equation

HRID 1155089 reaction equation
[NH:1]([C:29]([O:31]CC1C=CC=CC=1)=O)[C@H:2]([C:8]([NH:10][C@H:11]([C:18]([N:20]1[CH2:28][CH2:27][CH2:26][CH2:25][C@@H:21]1[C:22]([NH2:24])=[O:23])=[O:19])[CH2:12][C:13]1[N:17]=[CH:16][NH:15][CH:14]=1)=[O:9])[CH2:3][CH2:4]C(=O)N>C(O)(=O)C.[Pd]>[NH:1]1[C:29](=[O:31])[CH2:4][CH2:3][C@H:2]1[C:8]([NH:10][C@H:11]([C:18]([N:20]1[CH2:28][CH2:27][CH2:26][CH2:25][C@@H:21]1[C:22]([NH2:24])=[O:23])=[O:19])[CH2:12][C:13]1[N:17]=[CH:16][NH:15][CH:14]=1)=[O:9]

Participants

4

Reactant 1

HCID 178513896HCID 178513896, compound

Product 1

HCID 178513940HCID 178513940, compoundYield 51%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

2.63 g (5 mmoles) of Z-Gln-His-D-Pip-NH2 are dissolved in 50 ml of acetic acid, 0.5 g of a 10% palladium-on-carbon catalyst are added, and hydrogen is bubbled through the mixture for one hour. The catalyst is filtered off, the filtrate is heated to 60°-70° C., maintained at this temperature for 30 minutes, and then evaporated in vacuo. The residue is dissolved in water, the solution is passed through Dowex 2 ion exchange resin in the OH cycle, and then evaporated. The resulting crude product is applied onto the top of a silica gel column, and the column is eluted with solvent mixture (1). The fractions which contain the pure product are combined and evaporated. The residue is dissolved in water, the solution is decolourized, filtered, and the clear filtrate is evaporated. The amorphous residue is dried in vacuo over phosphorous pentoxide. 704 mg (51%) of Glp-His-D-Pip-NH2 are obtained; Rf4 =0.10; [α]D25 =+16.0° (c=1%, in water). Amino acid analysis: Glu: 1.03 (1.0), His: 1.00 (1.0), Pip: 0.96 (1.0).

Workup

  1. customhydrogen is bubbled through the mixture for one hour
  2. filtrationThe catalyst is filtered off
  3. temperaturethe filtrate is heated to 60°-70° C.
  4. temperaturemaintained at this temperature for 30 minutes
  5. customevaporated in vacuo
  6. dissolutionThe residue is dissolved in water
  7. customevaporated
  8. washthe column is eluted with solvent mixture (1)
  9. customevaporated
  10. dissolutionThe residue is dissolved in water
  11. filtrationfiltered
  12. customthe clear filtrate is evaporated
  13. dry with materialThe amorphous residue is dried in vacuo over phosphorous pentoxide

Sources & evidence

ORD record
ord-30f50c5b0b724c338bb2a2e8fbc634df
Source dataset
uspto-grants-1981_11
Patent number
US04299821

Reaction notes

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