反応 #62778

反応方程式

diisopropyl ether

anisole

trifluoroacetic acid

benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-(1-methyl-1-pyrrolidiniomethyl)-3-cephem-4-carboxylate trifluoroacetate

→

7-[2-(2-aminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-(1-methyl-1-pyrrolidiniomethyl)-3-cephem-4-carboxylate

収率 72.4%

溶媒

methylene chloride

反応条件

後処理

1. 1
   その他the resultant precipitates
2. 2
   ろ過were collected by filtration
3. 3
   洗浄washed with diisopropyl ether
4. 4
   workup.DISSOLUTIONdissolved in water (400 ml)
5. 5
   洗浄the elution
6. 6
   workup.ADDITIONThe fractions containing the object compound
7. 7
   その他were collected
8. 8
   濃縮concentrated in vacuo

実験手順

A solution of benzhydryl 7-[2-(2-tritylaminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-(1-methyl-1-pyrrolidiniomethyl)-3-cephem-4-carboxylate trifluoroacetate (syn isomer) (1.25 g) in methylene chloride (4 ml) was stirred at 0°-5° C., and anisole (2.6 ml) and trifluoroacetic acid (5.2 ml) were added thereto. The mixture was stirred for one hour at 0°-5° C. To the reaction mixture was added diisopropyl ether, and the resultant precipitates were collected by filtration, washed with diisopropyl ether and dissolved in water (400 ml). The solution was subjected to column chromatography on macroporus non-ionic adsorption resin "Diaion HP-20" and the elution was carried out with 30% aqueous solution of methanol. The fractions containing the object compound were collected, concentrated in vacuo and lyophilized to give 7-[2-(2-aminothiazol-4-yl)-2-difluoromethoxyiminoacetamido]-3-(1-methyl-1-pyrrolidiniomethyl)-3-cephem-4-carboxylate (syn isomer) (450 mg).

出典