(S)-N-tert-butyl-3,3-dimethyl-2-(1-phenylethylimino)-butyramide → (S)-N-tert-butyl-tert-leucinamide

HRID 726876Notes

Reaction equation

HRID 726876 reaction equation
[C:1]([NH:5][C:6](=[O:21])[C:7](=[N:12][C@H](C1C=CC=CC=1)C)[C:8]([CH3:11])([CH3:10])[CH3:9])([CH3:4])([CH3:3])[CH3:2]>CO.[Pd]>[C:1]([NH:5][C:6](=[O:21])[C@H:7]([C:8]([CH3:11])([CH3:10])[CH3:9])[NH2:12])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 1

HCID 54448077(S)-N-tert-butyl-3,3-dimethyl-2-(1-phenylethylimino)-butyramide

Product 1

HCID 13995173(S)-N-tert-butyl-tert-leucinamideYield 66%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 20.0 g (69.3 mmol) of (S)-N-tert-butyl-3,3-dimethyl-2-(1-phenylethylimino)-butyramide in 155 ml of methanol was hydrogenated in a low pressure hydrogenation apparatus in the presence of 12.5 g of 5 percent Pd/C at 40° C. and normal pressure for 51 hours. After cooling the catalyst was filtered off and the filtrate was evaporated to dryness: 11.9 g (92.2%) of white crystals containing 94.4% (S)-N-tert-butyl-tert-leucinamide, 92.5% e.e. Recrystallization from 50 ml of hexane yielded 7.8 g (66.0%) of (S)-N-tert-butyl-tert-leucinamide as white crystals, m.p. 78°-80° C., [α]=-32.2 (c=1, CHCl3), >98% e.e.

Workup

  1. temperatureAfter cooling the catalyst
  2. filtrationwas filtered off
  3. customthe filtrate was evaporated to dryness
  4. addition11.9 g (92.2%) of white crystals containing 94.4% (S)-N-tert-butyl-tert-leucinamide, 92.5% e.e
  5. customRecrystallization from 50 ml of hexane

Sources & evidence

ORD record
ord-cd921050bc5a4cec8ef982d2473b70dd
Source dataset
uspto-grants-1998_01
Patent number
US05710322

Reaction notes

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