(2S)-2-Amino-N,3,3-trimethylbutanamide → L-tert-Leucine

HRID 726878Notes

Reaction equation

HRID 726878 reaction equation
CN[C:3](=[O:10])[C@H:4]([C:6]([CH3:9])([CH3:8])[CH3:7])[NH2:5].Cl.CC(O)=[O:14]>>[NH2:5][C@H:4]([C:3]([OH:10])=[O:14])[C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

3

Reactant 2

HCID 445856(2S)-2-Amino-N,3,3-trimethylbutanamideHCID 22641269Acetate-hydrochloric acid

Product 1

HCID 164608L-tert-LeucineYield 41%

Procedure

A solution of (S)-N-methyl-tert-leucinamide in 100 ml of a 6N solution of HCl/CH3COOH (1:1) was heated under reflux for 14 days. Then, the mixture was evaporated, the residue was chromatographic over AMBERLITE. Evaporation and drying gave 750 mg (41%) of (S)-tert-leucine, [α]=+6.2 (c=1.62, 5N HCl), 97% e.e.

Workup

  1. temperatureunder reflux for 14 days
  2. customThen, the mixture was evaporated
  3. customEvaporation
  4. customdrying

Sources & evidence

ORD record
ord-b9447329890e458a93cc64d9374755eb
Source dataset
uspto-grants-1998_01
Patent number
US05710322

Reaction notes

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