反応 #40681

反応方程式

N-(benzyloxycarbonyl)-DL-asparagine

ethyl acetate

acetonitrile

iodosobenzene diacetate

→

2-benzyloxycarbonylamino-3-tert-butoxycarbonylaminopropionic acid

溶媒

water

反応条件

後処理

1. 1
   ろ過The reaction mixture was filtered
2. 2
   洗浄after washing the obtained solid with ethyl acetate, dioxane (180 ml), water (40 ml), 1N aqueous sodium hydroxide solution (10 ml) and di-t-butyl dicarbonate (6.1 g)
3. 3
   workup.ADDITIONwere added
4. 4
   workup.STIRRINGthe mixture was stirred overnight at room temperature
5. 5
   workup.ADDITIONThe reaction mixture was diluted with ethyl acetate
6. 6
   洗浄washed with 0.5N hydrochloric acid
7. 7
   その他The solvent was evaporated

実験手順

To N-(benzyloxycarbonyl)-DL-asparagine (7.5 g) were added ethyl acetate (36 ml), acetonitrile (36 ml), water (18 ml) and iodosobenzene diacetate (10 g), and the mixture was stirred overnight at room temperature. The reaction mixture was filtered and, after washing the obtained solid with ethyl acetate, dioxane (180 ml), water (40 ml), 1N aqueous sodium hydroxide solution (10 ml) and di-t-butyl dicarbonate (6.1 g) were added, and the mixture was stirred overnight at room temperature. The reaction mixture was diluted with ethyl acetate and washed with 0.5N hydrochloric acid. The solvent was evaporated to give 2-benzyloxycarbonylamino-3-tert-butoxycarbonylaminopropionic acid as a crude product. The crude product was treated in the same manner as in Step 1 of Example 15 to give (2-benzyloxycarbonylamino-3-hydroxypropyl)carbamic acid tert-butyl ester (2 g).

出典