HCID 131731169, compound → cyclo-L-Lys(Boc)-L-Glu(OH)

HRID 474181Notes

Reaction equation

HRID 474181 reaction equation
[NH:1]1[C:31](=[O:32])[C@H:18]([CH2:19][CH2:20][C:21](=[O:30])[O:22]CC2C=CC=CC=2)[NH:17][C:15](=[O:16])[C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9]>C(O)C(F)(F)F.[Pd]>[NH:1]1[C:31](=[O:32])[C@H:18]([CH2:19][CH2:20][C:21](=[O:22])[OH:30])[NH:17][C:15](=[O:16])[C@@H:2]1[CH2:3][CH2:4][CH2:5][CH2:6][NH:7][C:8]([O:10][C:11]([CH3:12])([CH3:13])[CH3:14])=[O:9]

Participants

4

Reactant 1

HCID 131731169HCID 131731169, compound

Product 1

HCID 131731170cyclo-L-Lys(Boc)-L-Glu(OH)

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 64092,2,2-TrifluoroethanolSolvent

Procedure

Cyclo-L-Lys(Boc)-L-Glu(OBzl) (22.2 g, 0.05 mol) was dissolved in 200 ml of trifluorethanol and 1.5 g of palladium black was added. Hydrogen was bubbled through the suspension with stirring for 48 hours. The reaction was monitored by TLC. After the reaction was complete, the catalyst was filtered off and the solvent was evaporated in vacuum. The residual peptide was dissolved in 200 ml of distilled water and the impurities were extracted with 3×100 ml of EtOAc. The water phase was combined and evaporated in vacuum. The precipitate was washed with ether and hexane and dried in air. The yield was 16.7 g (90%). Rf=0.4 (CHCl3:EtOAc:MeOH:32% AcOH=6:3:1:0.1); HPLC data: retention time 12.7 min.

Workup

  1. customHydrogen was bubbled through the suspension
  2. filtrationthe catalyst was filtered off
  3. customthe solvent was evaporated in vacuum
  4. dissolutionThe residual peptide was dissolved in 200 ml of distilled water
  5. extractionthe impurities were extracted with 3×100 ml of EtOAc
  6. customevaporated in vacuum
  7. washThe precipitate was washed with ether and hexane
  8. customdried in air

Sources & evidence

ORD record
ord-03ffb4e598ee417da158239bee92e0e3
Source dataset
uspto-grants-2014_01
Patent number
US08637521B2

Reaction notes

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