Methyl iodide → Methyl N-(tert-butoxycarbonyl)-L-threoninate

HRID 2285378Notes

Reaction equation

HRID 2285378 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([C@H:13]([OH:15])[CH3:14])[C:10]([OH:12])=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[C:16](=O)([O-])[O-].[K+].[K+].IC>CN(C)C=O.O>[CH3:16][O:11][C:10](=[O:12])[C@@H:9]([NH:8][C:6]([O:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])[C@H:13]([OH:15])[CH3:14]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 2724766N-tert-Butoxycarbonyl-L-threonine

Product 1

HCID 11368286Methyl N-(tert-butoxycarbonyl)-L-threoninateYield 87%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

(2S,3R)-2-tert-Butoxycarbonylamino-3-hydroxy-butyric acid (2 g, 9.12 mmol) was dissolved in N,N-dimethylformamide (15 mL), under an atmosphere of nitrogen. Potassium carbonate (2.02 g, 14.6 mmol) was added and the reaction was cooled using an ice bath. Iodomethane (679 μL, 10.9 mmol) was added and the reaction was stirred for 2 h, and allowed to slowly warm to room temperature. The reaction mixture was diluted with water and extracted with diethyl ether. The organic phase was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated to afford the title compound (1.85 g, 87%) as a colourless oil. 1H NMR (300 MHz, CDCl3) δ 1.26 (d, J=6.6 Hz, 3H), 1.47 (s, 9H), 2.24-2.45 (m, 1H), 3.78 (s, 3H), 4.15-4.37 (m, 2H), 5.21-5.45 (m, 1H). LCMS (m/z) 234.0 [M+H], Tr=1.57 min.

Workup

  1. temperaturethe reaction was cooled
  2. extractionextracted with diethyl ether
  3. washThe organic phase was washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-ea63123211914f51b796981c82988f47
Source dataset
uspto-grants-2015_09
Patent number
US09145441B2

Reaction notes

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