(3R,4S,5S)-tert-butyl 4-((S)-2-(((benzyloxy)carbonyl)amino)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoate → (3R,4S,5S)-tert-butyl 4-((S)-2-amino-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoate

HRID 879233Notes

Reaction equation

HRID 879233 reaction equation
[C:1]([O:5][C:6](=[O:35])[CH2:7][C@@H:8]([O:33][CH3:34])[C@@H:9]([N:14]([C:16](=[O:32])[C@H:17]([CH:29]([CH3:31])[CH3:30])[NH:18]C(OCC1C=CC=CC=1)=O)[CH3:15])[C@@H:10]([CH3:13])[CH2:11][CH3:12])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([O:5][C:6](=[O:35])[CH2:7][C@@H:8]([O:33][CH3:34])[C@@H:9]([N:14]([CH3:15])[C:16](=[O:32])[C@H:17]([CH:29]([CH3:30])[CH3:31])[NH2:18])[C@@H:10]([CH3:13])[CH2:11][CH3:12])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 10529182(3R,4S,5S)-tert-butyl 4-((S)-2-(((benzyloxy)carbonyl)amino)-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoate2×

Product 1

HCID 10546343(3R,4S,5S)-tert-butyl 4-((S)-2-amino-N,3-dimethylbutanamido)-3-methoxy-5-methylheptanoate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

500 mg (1 mmol) tert.-butyl-(3R,4S,5S)-4-[{N-[(benzyloxy)carbonyl]-L-valyl}(methyl)amino]-3-methoxy-5-methylheptanoate (intermediate 1) were dissolved in 50 ml Methanol and, after adding 100 mg 10% Palladium on activated carbon, was hydrated at RT for 1 h under atmospheric pressure. The catalyst was then filtered off and the solving agents was removed in a vacuum. 370 mg (quant.) of the title compound were obtained an almost colorless oil.

Workup

  1. filtrationThe catalyst was then filtered off
  2. customthe solving agents was removed in a vacuum

Sources & evidence

ORD record
ord-7426568f3f024c88a76476761a50338d
Source dataset
uspto-grants-2015_03
Patent number
US08987209B2

Reaction notes

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