Acetic Anhydride → Lacosamide

HRID 389388Notes

Reaction equation

HRID 389388 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]>C(Cl)Cl>[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 (5 g), was mixed with DCM (25 ml) at ambient temperature and stirred for 10 minutes to get a clear solution. To this solution, dimethylaminopyridine (0.025 g) was added at ambient temperature. Acetic anhydride (2.695 g) was slowly added over 10-12 minutes at ambient temperature. The solution was stirred for 30 minutes at room temperature. The reaction mixture was washed with 5% sodium bicarbonate (15 ml) solution, deionized water (15 ml), and brine (10 ml). The layers were separated and solvent was completely recovered under vacuum at 35° C. to 40° C. to get crude product. Yield=5.9 gm.

Workup

  1. customto get a clear solution
  2. stirringThe solution was stirred for 30 minutes at room temperature
  3. washThe reaction mixture was washed with 5% sodium bicarbonate (15 ml) solution
  4. customThe layers were separated
  5. customsolvent was completely recovered under vacuum at 35° C. to 40° C.
  6. customto get crude product

Sources & evidence

ORD record
ord-626c531670e14e75bb3b17188d5eae5d
Source dataset
uspto-grants-2013_02
Patent number
US08378142B2

Reaction notes

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