反応 #567145

反応方程式

water

ammonium formate

N-[5-((1R)-2-{benzyl-[1-(4-butoxy-benzenesulfonyl)-azetidin-3-yl]-amino}-1-triethylsilanyloxy-ethyl)-2-benzyloxy-phenyl]-methanesulfonamide

tetrabutylammonium fluoride

→

off-white solid

収率 89.2%

N-(5-{2-[1-(4-Butoxy-benzenesulfonyl)-azetidin-3-ylamino]-1-hydroxy-ethyl)-2-hydroxy-phenyl)-methanesulfonamide

収率 89.2%

溶媒

methanol

tetrahydrofuran

反応条件

後処理

1. 1
   抽出extracted with ethyl acetate
2. 2
   乾燥The organic solution was dried over anhydrous sodium sulfate
3. 3
   その他evaporated
4. 4
   その他The residue obtained
5. 5
   温度at reflux for 18 h
6. 6
   ろ過filtered through Celite
7. 7
   洗浄eluted with more methanol
8. 8
   その他The filtrate was evaporated
9. 9
   洗浄the residue washed with ether-hexanes

実験手順

To a solution of N-[5-((1R)-2-{benzyl-[1-(4-butoxy-benzenesulfonyl)-azetidin-3-yl]-amino}-1-triethylsilanyloxy-ethyl)-2-benzyloxy-phenyl]-methanesulfonamide (0.10 g, 0.12 mmol) in tetrahydrofuran (1 ml) was added 0.2 ml of tetrabutylammonium fluoride (1 M in THF). After 2 h at room temperature, the mixture was treated with water and extracted with ethyl acetate. The organic solution was dried over anhydrous sodium sulfate, and evaporated. The residue obtained was dissolved in methanol (3 ml), and treated with ammonium formate (0.12 g, 1.8 mmol) and 10% Pd/C (20 mg) at reflux for 18 h. It was then cooled to room temperature, filtered through Celite, and eluted with more methanol. The filtrate was evaporated, and the residue washed with ether-hexanes to give 55 mg of an off-white solid; m.p. 67-70° C.; MS (ES) m/z 514.0 (MH+); HRMS (FAB) Calcd. for C22H32N3O7S2 (MH+): 514.1682, Found: 514.1693.

出典