(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 882574Notes

Reaction equation

HRID 882574 reaction equation
C(OC([NH:11][C@H:12]([C:16]([N:18]([CH3:35])[C@@H:19]([C@@H:31]([CH3:34])[CH2:32][CH3:33])[C@H:20]([O:29][CH3:30])[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[O:17])[CH:13]([CH3:15])[CH3:14])=O)C1C=CC=CC=1>CO.[Pd]>[CH3:30][O:29][C@@H:20]([C@@H:19]([N:18]([CH3:35])[C:16](=[O:17])[C@H:12]([CH:13]([CH3:15])[CH3:14])[NH2:11])[C@@H:31]([CH3:34])[CH2:32][CH3:33])[CH2:21][C:22]([O:24][C:25]([CH3:28])([CH3:26])[CH3:27])=[O:23]

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) of tert-butyl (3R,4S,5S)-4-[{N-[(benzyloxy)carbonyl]-L-valyl}(methyl)amino]-3-methoxy-5-methylheptanoate (intermediate 1) were dissolved in 50 ml of methanol and, after addition of 100 mg of 10% palladium on activated carbon, hydrogenated under standard hydrogen pressure at RT for 1 h. The catalyst was then filtered off and the solvent was removed under reduced pressure. This gave 370 mg (quant.) of the title compound as a virtually colourless oil.

Workup

  1. customat RT
  2. customfor 1 h
  3. filtrationThe catalyst was then filtered off
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-658cf7c2dd8b4588b39bcea39341fcb2
Source dataset
uspto-grants-2015_03
Patent number
US08992932B2

Reaction notes

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