Reaction #502083

ord-0a66b2c927b04473a72ca051f029c794

Reaction equation

COC(=O)[C@H](CCCCNC(=O)OCc1ccccc1)NC(=O)OC(C)(C)C
Boc-Lys(Cbz)-OMe
CCOC(C)=O
Ethyl acetate
→
COC(=O)[C@H](CCCCN)NC(=O)OC(C)(C)C
Boc-Lys-OMe

Reactants

COC(=O)[C@H](CCCCNC(=O)OCc1ccccc1)NC(=O)OC(C)(C)C
Boc-Lys(Cbz)-OMe
CCOC(C)=O
Ethyl acetate

Reagents

[Pd]
Palladium

Solvents

CO
MeOH

Conditions

Detailed conditions
See reaction.notes.procedure_details.

Workup

  1. 1
    FiltrationThe organic solution was filtered through Celite
  2. 2
    Washwashed with 10 mL MeOH
  3. 3
    OtherThe filtrate was evaporated under reduced pressure

Procedure

1.0 g of Boc-Lys(Cbz)-OMe (5) was dissolved in 40 mL MeOH:Ethyl acetate. 100 mg of Palladium on active carbon (Pd/C) was added to the solution. The solution was stirred under hydrogen for 2 hrs. The organic solution was filtered through Celite and washed with 10 mL MeOH. The filtrate was evaporated under reduced pressure to yield Boc-Lys-OMe of formula (6)

Source

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08088757B2uspto-grants-2012_01