HCID 131736616, compound → HCID 13979009, compound

HRID 1481075Notes

Reaction equation

HRID 1481075 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 131736616HCID 131736616, compound

Product 1

HCID 13979009HCID 13979009, compoundYield 79.4%

Reagents, catalysts & solvents 2

HCID 9942167Palladium hydroxideCatalystHCID 702EthanolSolvent

Procedure

A mixture of tert-butyl (2R,3S,αS)-3-(N-benzyl-N-α-methylbenzylamino)-2-methyl-butyrate (458 mg, 1.25 mmol) and 20% Pd(OH)2 on carbon (200 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 172 mg of the title compound, which was used in the next step without purification. 1H NMR (CDCl3, 200 MHz): δ=8.4 (broad), 3.45-3.65 (m, 1H), 2.70-2.80 (m, 1H), 1.46 (s, 9H), 1.42 (d, 3H, J=7.0 Hz), 1.29 (d, 3H, J=7.0 Hz).

Workup

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

Sources & evidence

ORD record
ord-e68305d4e5cf4c66b914dd7439b34960
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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