Ethyl Acetate → (S)-Methyl 6-amino-2-((tert-butoxycarbonyl)amino)hexanoate

HRID 414901Notes

Reaction equation

HRID 414901 reaction equation
[NH:1]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:2]([C:18]([O:20][CH3:21])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH:7]C(OCC1C=CC=CC=1)=O.C(OCC)(=O)C>CO.[Pd]>[NH:1]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C@H:2]([C:18]([O:20][CH3:21])=[O:19])[CH2:3][CH2:4][CH2:5][CH2:6][NH2:7]

Participants

5

Reactant 2

HCID 8857Ethyl AcetateHCID 11132998Boc-L-Lys(Z)-OMe

Product 1

HCID 7018772(S)-Methyl 6-amino-2-((tert-butoxycarbonyl)amino)hexanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

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)

Workup

  1. filtrationThe organic solution was filtered through Celite
  2. washwashed with 10 mL MeOH
  3. customThe filtrate was evaporated under reduced pressure

Sources & evidence

ORD record
ord-0a66b2c927b04473a72ca051f029c794
Source dataset
uspto-grants-2012_01
Patent number
US08088757B2

Reaction notes

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