HCID 131736615, compound → HCID 89813006, compound

HRID 1481073Notes

Reaction equation

HRID 1481073 reaction equation
C([N:8]([C@@H:17]([CH3:27])[C@H:18]([CH3:26])[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[C@@H](C)C1C=CC=CC=1)C1C=CC=CC=1>CCO.[OH-].[OH-].[Pd+2]>[C:22]([O:21][C:19](=[O:20])[C@@H:18]([CH3:26])[C@@H:17]([NH2:8])[CH3:27])([CH3:24])([CH3:23])[CH3:25]

Participants

4

Reactant 1

HCID 131736615HCID 131736615, compound

Product 1

HCID 89813006HCID 89813006, compoundYield 74.3%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl (2S,3S,αS)-3-(N-benzyl-N-α-methylbenzylamino)-2-methyl-butyrate (245 mg, 0.668 mmol) and 20% Pd(OH)2 on carbon (100 mg) in EtOH (10 mL) was stirred under H2 atmosphere (1 atm) for 48 h, then filtered through a pad of Celite. The filtrate was concentrated to give 86 mg of the title compound, which was used in the next step without purification. 1H NMR (CDCl3, 200 MHz): δ=5.5 (broad), 3.45-3.65 (m, 1H), 2.60-2.75 (m, 1H), 1.46 (s, 9H), 1.36 (d, 3H, J=6.6 Hz), 1.26 (d, 3H, J=7.0 Hz).

Workup

  1. filtrationfiltered through a pad of Celite
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9ac8cbd730bc4fbd9cac5ad6b4b4b9f5
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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