HCID 131713001, compound → HCID 13312531, compound

HRID 851714Notes

Reaction equation

HRID 851714 reaction equation
[N:1]1(C(OCC2C=CC=CC=2)=O)[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:9][C@H:10]([C:15]([N:17]1[CH2:25][CH2:24][CH2:23][CH2:22][C@H:18]1[C:19]([NH2:21])=[O:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8]>CO.[Pd]>[NH:1]1[C:5](=[O:6])[CH2:4][CH2:3][C@H:2]1[C:7]([NH:9][C@H:10]([C:15]([N:17]1[CH2:25][CH2:24][CH2:23][CH2:22][C@H:18]1[C:19]([NH2:21])=[O:20])=[O:16])[CH2:11][CH:12]([CH3:14])[CH3:13])=[O:8]

Participants

4

Reactant 1

HCID 131713001HCID 131713001, compound

Product 1

HCID 13312531HCID 13312531, compoundYield 87.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

2.1 g (4.32 mmoles) of Z-Glp-Leu-Pip-NH2 are dissolved in 40 ml of methanol. 0.2 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 evaporated, and the residue is triturated with ether. The resulting crude product (1.48 g) is dissolved in 20 ml of water, the solution is decolourized, filtered, and 4 g of sodium chloride are dissolved in the clear filtrate. The aqueous solution is extracted thrice with 10 ml of chloroform, each. The chloroform solutions are combined, dried over anhydrous sodium sulfate, evaporated, and the amorphous residue is triturated with a mixture of ethyl acetate and ether. 1.33 g (87.5%) of Glp-Leu-Pip-NH2 are obtained; Rf5 =0.60, [α]D25 =-86.4° (c=1%, in acetic acid).

Workup

  1. customhydrogen is bubbled through the mixture for one hour
  2. filtrationThe catalyst is filtered off
  3. customthe filtrate is evaporated
  4. customthe residue is triturated with ether
  5. dissolutionThe resulting crude product (1.48 g) is dissolved in 20 ml of water
  6. filtrationfiltered
  7. dissolution4 g of sodium chloride are dissolved in the clear filtrate
  8. extractionThe aqueous solution is extracted thrice with 10 ml of chloroform
  9. dry with materialdried over anhydrous sodium sulfate
  10. customevaporated
  11. customthe amorphous residue is triturated with a mixture of ethyl acetate and ether

Sources & evidence

ORD record
ord-713583045a714583adda0d0051277872
Source dataset
uspto-grants-1983_05
Patent number
US04386073

Reaction notes

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