反応 #451736

反応方程式

4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-n-propoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate

methanol

water

→

7-[2-(2-formamidothiazol-4-yl)-2-n-propoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid

収率 85.7%

溶媒

tetrahydrofuran

反応条件

後処理

1. 1
   その他was subjected to catalytic reduction under ordinary pressure at room temperature
2. 2
   その他After removing insoluble substance
3. 3
   ろ過by filtration
4. 4
   濃縮the filtrate was concentrated in vacuo
5. 5
   workup.ADDITIONWater and ethyl acetate were added to the residue
6. 6
   その他The insoluble substance was removed by filtration
7. 7
   その他the aqueous layer was separated
8. 8
   workup.ADDITIONEthyl acetate was added to the solution
9. 9
   抽出extracted with ethyl acetate
10. 10
    抽出The ethyl acetate solution and extract
11. 11
    洗浄washed with a saturated aqueous solution of sodium chloride
12. 12
    乾燥dried over magnesium sulfate
13. 13
    濃縮The solution was concentrated in vacuo
14. 14
    その他the residue was triturated with diethyl ether
15. 15
    ろ過collected by filtration

実験手順

A suspension of 4-nitrobenzyl 7-[2-(2-formamidothiazol-4-yl)-2-n-propoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylate (syn isomer, 2.4 g.), 10% palladium carbon (1.0 g.), methanol (24 ml.), water (3.6 ml.) and tetrahydrofuran (48 ml.) was subjected to catalytic reduction under ordinary pressure at room temperature. After removing insoluble substance by filtration, the filtrate was concentrated in vacuo. Water and ethyl acetate were added to the residue, and subjected to pH 8 with a saturated aqueous solution of sodium bicarbonate. The insoluble substance was removed by filtration, and the aqueous layer was separated. Ethyl acetate was added to the solution, adjusted to pH 2.0 with hydrochloric acid and extracted with ethyl acetate. The ethyl acetate solution and extract were combined together, washed with a saturated aqueous solution of sodium chloride and dried over magnesium sulfate. The solution was concentrated in vacuo, and the residue was triturated with diethyl ether and collected by filtration to give 7-[2-(2-formamidothiazol-4-yl)-2-n-propoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 1.6 g.).

出典