反応 #96107

反応方程式

water

triethylamine

p-nitrobenzyl α-[3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-α-(1-hydroxyethylidene)acetate

toluene-p-sulfonyl chloride

→

p-nitrobenzyl α-[3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-α-(1-toluene-p-sulfonyloxyethylidene)acetate

収率 51.6%

溶媒

dimethylformamide

反応条件

後処理

1. 1
   温度to warm slowly up to room temperature
2. 2
   抽出extracted with ethyl acetate
3. 3
   洗浄The extract solution is washed with water
4. 4
   その他dried
5. 5
   その他evaporated
6. 6
   その他The obtained residue is chromatographed over silica gel containing 10% water

実験手順

To a solution of p-nitrobenzyl α-[3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-α-(1-hydroxyethylidene)acetate (940 mg) in dimethylformamide containing 10% tetrahydrofuran (5 ml) is added toluene-p-sulfonyl chloride (456 mg). After cooling to -70° C., the solution is mixed with triethylamine(0.3 ml). The reaction mixture is allowed to warm slowly up to room temperature, poured into water, and extracted with ethyl acetate. The extract solution is washed with water, dried, and evaporated. The obtained residue is chromatographed over silica gel containing 10% water using benzene containing 5% ethyl acetate to give p-nitrobenzyl α-[3-phenoxymethyl-7-oxo-4-thia-2,6-diazabicyclo[3,2,0]hept-2-en-6-yl]-α-(1-toluene-p-sulfonyloxyethylidene)acetate (644 mg). IR: νmaxCHCl3 1785, 1735 cm-1. NMR: δCDCl3 2.45s3H, 4.75+4.20ABq (14 Hz)2H, 5.15s2H, 5.77s2H, 8.30-6.60 ml 3H.

出典