HCID 54465968, compound → (2S)-2-Amino-N,3,3-trimethylbutanamide

HRID 726874Notes

Reaction equation

HRID 726874 reaction equation
[CH3:1][C:2]([CH3:18])([CH3:17])[C:3](=[N:8][C@H](C1C=CC=CC=1)C)[C:4]([NH:6][CH3:7])=[O:5]>CO.[Pd]>[CH3:7][NH:6][C:4](=[O:5])[C@H:3]([C:2]([CH3:18])([CH3:17])[CH3:1])[NH2:8]

Participants

4

Reactant 1

HCID 54465968HCID 54465968, compound

Product 1

HCID 445856(2S)-2-Amino-N,3,3-trimethylbutanamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 100.0 g (406 mmol) of (S)-3,3,N-trimethyl-2-(1-phenylethylimino)-butyramide in 775 ml of methanol was hydrogenated in a 21 autoclave in the presence of 5 g of 5 percent Pd/C at 40° C. and at a pressure of 1 bar for 7 hours. Re-hydrogenation was carried out for 6 hours at 70° C. and under a pressure of 2 bar in order to complete the hydrogenolysis. After cooling the catalyst was filtered off and the filtrate was evaporated to dryness: 58.3 g (99.6%) of white crystals with 99.6% N-methyl-tert-leucinamide content, e.e. 97.2%. Recrystallization from 425 ml of cyclohexane yields (S)-N-methyl-tert-leucinamide as white crystals, m.p. 90°-93° C., [α]=-40.8 (c=1, CHCl3), 99.3% e.e. In order to determine the e.e value, the product was derivatized with (-)-camphanoyl chloride and the diastereomer mixture was analyzed by gas chromatography.

Workup

  1. temperatureAfter cooling the catalyst
  2. filtrationwas filtered off
  3. customthe filtrate was evaporated to dryness
  4. customRecrystallization from 425 ml of cyclohexane

Sources & evidence

ORD record
ord-ea5538a4bb6e4db0bd8392298e151457
Source dataset
uspto-grants-1998_01
Patent number
US05710322

Reaction notes

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