反応 #336779

反応方程式

7β-phenylacetamido-3-(1,2,3-triazol-4-ylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester

pyridine

trityl chloride

pyridine

phosphorus pentachloride

hydrochloric acid

1.3-butanediol

→

7β-amino-3-(trityl-1,2,3-triazol-4-ylthiomethylthio) -3-cephem-4- carboxylic acid diphenylmethyl ester

収率 56.0%

溶媒

dichloromethane

dichloromethane

dichloromethane

water

dichloromethane

water

反応条件

後処理

1. 1
   抽出extracted with ethyl acetate
2. 2
   洗浄The extract is washed with water
3. 3
   乾燥dried over sodium sulfate
4. 4
   濃縮concentrated
5. 5
   workup.STIRRINGthe mixture is stirred for 30 minutes
6. 6
   workup.STIRRINGthe mixture is stirred at -20 to -30° C. for 10 minutes and under ice cooling for 40 minutes
7. 7
   洗浄washed with brine
8. 8
   乾燥dried over sodium sulfate
9. 9
   濃縮concentrated
10. 10
    洗浄washed with ether
11. 11
    workup.DISSOLUTIONdissolved in dichloromethane
12. 12
    洗浄washed with 5% aqueous sodium hydrogen carbonate
13. 13
    乾燥dried over sodium sulfate
14. 14
    濃縮concentrated
15. 15
    その他The residue is purified by silica gel chromatography (toluene : ethyl acetate=2:1)

実験手順

To a solution of 7β-phenylacetamido-3-(1,2,3-triazol-4-ylthiomethylthio)-3-cephem-4-carboxylic acid diphenylmethyl ester (10.0 g : 15.9 mMol.) in dichloromethane (100 ml) under ice cooling are added pyridine (1.54 ml : 19.1 mMol.) and trityl chloride (5.32 g 19.1 mMol.), and the mixture is stirred at room temperature for 1 hour. The reaction mixture is mixed with 10% hydrochloric acid (2 ml), diluted with water, and extracted with ethyl acetate. The extract is washed with water, dried over sodium sulfate, and concentrated. To a solution of the residue in dichloromethane (50 ml) under ice cooling are added pyridine (2.57 ml : 31.8 mMol.) and phosphorus pentachloride (5.96 g : 28.6 mMol.), and the mixture is stirred for 30 minutes. The reaction mixture is added dropwise to a solution of 1.3-butanediol (8.6 ml : 95.9 mMol.) in dichloromethane (25 ml) at -30° C. , and the mixture is stirred at -20 to -30° C. for 10 minutes and under ice cooling for 40 minutes. The reaction mixture is mixed with water, diluted with dichloromethane, washed with brine, dried over sodium sulfate, and concentrated. The residue is pulverized with ether, washed with ether, dissolved in dichloromethane, washed with 5% aqueous sodium hydrogen carbonate, dried over sodium sulfate, and concentrated. The residue is purified by silica gel chromatography (toluene : ethyl acetate=2:1) to give 7β-amino-3-(trityl-1,2,3-triazol-4-ylthiomethylthio) -3-cephem-4- carboxylic acid diphenylmethyl ester (6.70 g : pale yellow foam. Yield: 56 %,

出典