(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 1022516Notes

Reaction equation

HRID 1022516 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 at RT under atmospheric pressure 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 an almost colourless oil.

Workup

  1. filtrationThe catalyst was then filtered off
  2. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-4cce2ff75d234e268a11d2cc0db43bd4
Source dataset
uspto-grants-2014_05
Patent number
US08722629B2

Reaction notes

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