N-[N-(benzyloxycarbonyl)-N-methylvalyl]-L-aspartic acid di-tert-butyl ester → N-(N-methyl-L-valyl)-L-aspartic acid di-tert-butyl ester

HRID 529213Notes

Reaction equation

HRID 529213 reaction equation
[C:1]([O:5][C:6](=[O:35])[C@H:7]([CH2:27][C:28]([O:30][C:31]([CH3:34])([CH3:33])[CH3:32])=[O:29])[NH:8][C:9](=[O:26])[C@H:10]([CH:23]([CH3:25])[CH3:24])[N:11](C(OCC1C=CC=CC=1)=O)[CH3:12])([CH3:4])([CH3:3])[CH3:2]>C(O)C.[Pd]>[C:1]([O:5][C:6](=[O:35])[C@H:7]([CH2:27][C:28]([O:30][C:31]([CH3:32])([CH3:34])[CH3:33])=[O:29])[NH:8][C:9](=[O:26])[C@H:10]([CH:23]([CH3:25])[CH3:24])[NH:11][CH3:12])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 1

HCID 86714692N-[N-(benzyloxycarbonyl)-N-methylvalyl]-L-aspartic acid di-tert-butyl ester

Product 1

HCID 86714693N-(N-methyl-L-valyl)-L-aspartic acid di-tert-butyl esterYield 100%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a solution of the compound (0.91 g, 1.8 mmol) obtained in step 1 in ethanol (40 ml) was added a catalytic amount of 10% palladium/carbon, and the mixture was stirred for 3 hours under a hydrogen atmosphere. The catalyst was filtered off, and the filtrate was concentrated under reduced pressure to give the title compound (0.66 g, 1.8 mmol, 99%).

Workup

  1. filtrationThe catalyst was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-79b3082c4df14b84bd64888bd9a6de48
Source dataset
uspto-grants-2016_05
Patent number
US09346821B2

Reaction notes

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