反应 #57044

反应方程式

Boc-Tyr-OH

N-hydroxysuccinamide

gabapentin

sodium hydroxide

→

Boc-Tyr Gabapentin

收率 106.7%

溶剂

acetonitrile

反应条件

后处理

1. 1
   workup.STIRRINGthe resulting mixture stirred at ambient temperature for 16 h
2. 2
   浓缩The reaction was concentrated under reduced pressure
3. 3
   workup.DISSOLUTIONthe residue was dissolved in ethyl acetate/diethyl ether (1/1, 200 mL)
4. 4
   洗涤washed with 0.1M aqueous potassium hydrogensulfate (2×200 mL)
5. 5
   其他The organic phase was separated
6. 6
   干燥dried over Na2SO4
7. 7
   过滤filtered
8. 8
   浓缩concentrated to dryness under reduced pressure

实验过程

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).

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