反応 #969857

反応方程式

4-(Tert-butoxycarbonylamino)-3-sulfobutanoic acid

HCl

Dioxane

maleic anhydride

→

title compound

収率 83.0%

(Z)-4-(3-carboxy-2-sulfopropylamino)-4-oxobut-2-enoic acid

収率 83.0%

溶媒

DMA

反応条件

後処理

1. 1
   その他evaporated
2. 2
   その他evaporated
3. 3
   洗浄eluted with water
4. 4
   その他crystallized with EtOH/Hexane

実験手順

4-(Tert-butoxycarbonylamino)-3-sulfobutanoic acid (321 mg, 1.13 mmol) was stirred in the mixture of HCl (conc)/Dioxane (1:4, 15 ml) for 30 min, evaporated and coevaporated with EtOH/Toluene (1:1, 4×20 ml) to dryness. To the dryness material was added maleic anhydride (121 mg, 1.23 mmol) and DMA (20 ml) and the mixture was stirred overnight, evaporated and run through C-18 column eluted with water and crystallized with EtOH/Hexane to afford 263 mg (83%) of the title compound. ESI MS 279.8 (M−H). The NMR data are the same through the route with 4-azido-3-sulfobutanoic acid.

出典