Acetic Anhydride → Lacosamide

HRID 420115Notes

Reaction equation

HRID 420115 reaction equation
[CH2:1]([NH:8][C:9](=[O:15])[C@@H:10]([CH2:12][O:13][CH3:14])[NH2:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CN(C1C=CC=CN=1)C.[C:25](OC(=O)C)(=[O:27])[CH3:26]>ClCCl>[CH3:26][C:25]([NH:11][C@@H:10]([C:9]([NH:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:15])[CH2:12][O:13][CH3:14])=[O:27]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 218852-DimethylaminopyridineHCID 10104501N-Benzyl-O-methyl-D-serinamide

Product 1

HCID 219078Lacosamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-benzyl-O-methyl-D-serinamide (92 g), was mixed with dichloromethane (368 ml) at ambient temperature and stirred for 10 minutes to get a clear solution. To this solution, dimethylaminopyridine (0.47 g) was added at ambient temperature. Acetic anhydride (45.09 g) was slowly added over 15-20 minutes at ambient temperature. The solution was stirred for 2 hours at room temperature. The reaction mixture was washed with sodium hydroxide (19.16 gm dissolved in 291 ml water), and deionized water (276 ml). The layers were separated and solvent was completely recovered under vacuum at 35-40° C. to get crude product. Yield=82.6 gm; Chiral purity=100%.

Workup

  1. customto get a clear solution
  2. stirringThe solution was stirred for 2 hours at room temperature
  3. washThe reaction mixture was washed with sodium hydroxide (19.16 gm dissolved in 291 ml water), and deionized water (276 ml)
  4. customThe layers were separated
  5. customsolvent was completely recovered under vacuum at 35-40° C.
  6. customto get crude product

Sources & evidence

ORD record
ord-ed0a4b6c54b54a6787b025c0d8a9c340
Source dataset
uspto-grants-2012_01
Patent number
US08093426B2

Reaction notes

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