반응 #305176

반응 방정식

sodium bicarbonate

Example 13

tert-butyl (−)-[(4aS*,5R*,8aS*)-8a-(5-amino-2-fluorophenyl)-5-methoxy-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]carbamate

[Bis(2-methoxyethyl)amino]sulfur trifluoride

tert-butyl [(4aR,6R,8aS)-8a-(5-nitro-2-fluorophenyl)-6-hydroxymethyl-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]carbamate

→

title compound

tert-butyl [(4aR,6R,8aS)-8a-(5-nitro-2-fluorophenyl)-6-fluoromethyl-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]carbamate

용매

dichloromethane

반응 조건

후처리

1. 1
   추출the aqueous layer was extracted with chloroform
2. 2
   건조The organic layer was dried over anhydrous magnesium sulfate
3. 3
   기타The solvent was evaporated under reduced pressure
4. 4
   기타the residue was purified by NH-silica gel column chromatography

실험 절차

[Bis(2-methoxyethyl)amino]sulfur trifluoride (285 μl) was added dropwise to a solution of tert-butyl [(4aR,6R,8aS)-8a-(5-nitro-2-fluorophenyl)-6-hydroxymethyl-4,4a,5,6,8,8a-hexahydro-7-oxa-3-thia-1-azanaphthalen-2-yl]carbamate obtained in Preparation Example 13 (575 mg) in dichloromethane (55 ml) at −78° C. The mixture was stirred overnight with gradual heating to room temperature. A sodium bicarbonate solution was added to the reaction solution, and the aqueous layer was extracted with chloroform. The organic layer was dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by NH-silica gel column chromatography to obtain the title compound (240 mg).

출처