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

HRID 1625694Notes

Reaction equation

HRID 1625694 reaction equation
C(OC([NH:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:17]([O:19][CH3:20])=[O:18])=O)C1C=CC=CC=1.[H][H]>CO.[Pd]>[NH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C@H:16]([NH:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])[C:17]([O:19][CH3:20])=[O:18]

Participants

5

Reactant 2

HCID 11132998Boc-L-Lys(Z)-OMeHCID 178418361HCID 178418361, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

(S)-methyl 6-(benzyloxycarbonylamino)-2-(tert-butoxycarbonylamino)hexanoate (8.60 g) was hydrogenated in 150 mL MeOH over 5% palladium on activated carbon (1.08 g) under 1 atm hydrogen at ambient temperature for 3 hours. The spent catalyst was removed by vacuum filtration through a celite pad which was washed with MeOH. The combined filtrate and wash were concentrated under reduced pressure, affording (S)-methyl 6-amino-2-(tert-butoxycarbonylamino)hexanoate (TU3000-128) as clear viscous oil. MS (ESI+): calcd. 261.17. found 261.20 (MH+). H-NMR (600 MHz, CDCl3):1.328 (2H, m), 1.375 (9H, s), 1.390 (2H, m), 1.55 (1H, m), 1.74(1H, m), 2.623(2H, d, J=6.9 Hz), 3.671 (3H, s), 4.237 (1H, m), 5.007 (1H, m).

Workup

  1. customThe spent catalyst was removed by vacuum filtration through a celite pad which
  2. washwas washed with MeOH
  3. washThe combined filtrate and wash
  4. concentrationwere concentrated under reduced pressure

Sources & evidence

ORD record
ord-27bbff46148b4fb1906df030379055b4
Source dataset
uspto-grants-2014_07
Patent number
US08785151B2

Reaction notes

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