反応 #490603

反応方程式

N-Boc-hydroxy proline

HATU

diisopropylethylamine

EtOAc

vinylcyclopropylammonium tosylate

diisopropylethylamine

EtOAc

→

oil

収率 85.0%

(2S,4R)-tert-butyl 2-((1R,2S)-1-(ethoxycarbonyl)-2-vinylcyclopropylcarbamoyl)-4-hydroxypyrrolidine-1-carboxylate

収率 85.0%

反応条件

後処理

1. 1
   workup.WAITAfter 3 h at 10° C.
2. 2
   ろ過the reaction slurry was filtered
3. 3
   洗浄the resulting cake was rinsed with EtOAc (2 L)
4. 4
   洗浄The resulting filtrate was washed with a 10% aqueous solution of NaCl (5×770 g)
5. 5
   ろ過The product-containing organic layer was filtered

実験手順

To a stiffing slurry of N-Boc-hydroxy proline (78 g), HATU (128 g), and EtOAc (558 g), at 0° C., was added diisopropylethylamine (65 g). After 45 min, a solution containing vinylcyclopropylammonium tosylate (100 g), diisopropylethylamine (65.0 g), and EtOAc (366 g) was added to the activated ester solution. After 3 h at 10° C., the reaction slurry was filtered and the resulting cake was rinsed with EtOAc (2 L). The resulting filtrate was washed with a 10% aqueous solution of NaCl (5×770 g). The product-containing organic layer was filtered, concentrated under reduced pressure to an oil (85% yield).

出典