Reaction #57044

Reaction equation

Boc-Tyr-OH

N-hydroxysuccinamide

gabapentin

sodium hydroxide

→

Boc-Tyr Gabapentin

Yield 106.7%

Solvents

acetonitrile

Conditions

Workup

1. 1
   workup.STIRRINGthe resulting mixture stirred at ambient temperature for 16 h
2. 2
   ConcentrationThe reaction was concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate/diethyl ether (1/1, 200 mL)
4. 4
   Washwashed with 0.1M aqueous potassium hydrogensulfate (2×200 mL)
5. 5
   OtherThe organic phase was separated
6. 6
   Dryingdried over Na2SO4
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated to dryness under reduced pressure

Procedure

To a solution of Boc-Tyr-OH (4.2 g, 15 mmol) in acetonitrile (100 mL) was added N-hydroxysuccinamide (1.84 g, 16 mmol) and N,N-dicyclohexylcarbodiimide (3.3 g, 16 mmol). The reaction was stirred at ambient temperature for 2 h. The reaction mixture was filtered directly into an aqueous solution (100 mL) of gabapentin (2.7 g, 16 mmol) and sodium hydroxide (640 mg, 16 mmol), and the resulting mixture stirred at ambient temperature for 16 h. The reaction was concentrated under reduced pressure, the residue was dissolved in ethyl acetate/diethyl ether (1/1, 200 mL) and washed with 0.1M aqueous potassium hydrogensulfate (2×200 mL). The organic phase was separated, dried over Na2SO4, filtered, and concentrated to dryness under reduced pressure to afford Boc-Tyr-Gabapentin as a white solid (7.4 g, 16 mmol).

Source