HCID 53842782, compound → (2S)-2-Amino-3,3-dimethylbutanamide

HRID 726877Notes

Reaction equation

HRID 726877 reaction equation
[CH3:1][C:2]([CH3:17])([CH3:16])[C:3](=[N:7][C@H](C1C=CC=CC=1)C)[C:4]([NH2:6])=[O:5]>CO.[Pd]>[NH2:7][C@H:3]([C:4]([NH2:6])=[O:5])[C:2]([CH3:17])([CH3:16])[CH3:1]

Participants

4

Reactant 1

HCID 53842782HCID 53842782, compound

Product 1

HCID 11297986(2S)-2-Amino-3,3-dimethylbutanamideYield 78.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 12.0 g (51.7 mmol) of (S)-3,3-dimethyl-2-(1-phenylethylimino)-butyramide in 200 ml of methanol was hydrogenated in a low pressure hydrogenation apparatus in the presence of 2.0 g of 5 percent Pd/C at 40° C. and normal pressure for 6.5 hours. After cooling the catalyst was filtered off and the filtrate was evaporated to dryness: 6.7 g (99.5%) of white crystals containing 90.8% (S)-tert-leucinamide, 97.0% e.e. Recrystallization from 40 ml of cyclohexane yielded 5.3 g (78.5%) of (S)-tert-leucinamide as white crystals, m.p. 104°-105° C., [α]=-23.2 (c=1, CHCl3), 96.9% e.e.

Workup

  1. temperatureAfter cooling the catalyst
  2. filtrationwas filtered off
  3. customthe filtrate was evaporated to dryness
  4. addition6.7 g (99.5%) of white crystals containing 90.8% (S)-tert-leucinamide, 97.0% e.e
  5. customRecrystallization from 40 ml of cyclohexane

Sources & evidence

ORD record
ord-b17eb69d6e4f402f9f0f89ab2362aa2f
Source dataset
uspto-grants-1998_01
Patent number
US05710322

Reaction notes

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