Boc-L-Lys(Z)-OMe → (S)-Methyl 6-amino-2-((tert-butoxycarbonyl)amino)hexanoate

HRID 538967Notes

Reaction equation

HRID 538967 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 1

HCID 11132998Boc-L-Lys(Z)-OMe

Product 1

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

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A total amount of Boc-Lys(Cbz)-OMe was dissolved in a mixed solvent of 40 ml of ethyl acetate and 40 ml of methanol, and then the resultant solution was stirred at room temperature for 4 hours under a hydrogen atmosphere while gradually adding 0.223 g of Pd/C. The reaction product was passed through 3.56 g of celite (Sigma Aldrich) to remove Pd/C, and was then washed with 20 ml of methanol (MeOH) two times to obtain a filtrate. The filtrate was evaporated to obtain light viscous solid Boc-Lys-OMe.

Workup

  1. customto remove Pd/C
  2. washwas then washed with 20 ml of methanol (MeOH) two times
  3. customto obtain a filtrate
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-a33d6444006d4b4c9a3a973342cc2b41
Source dataset
uspto-grants-2014_10
Patent number
US08865935B2

Reaction notes

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