反応 #47740

反応方程式

trityl chloride

water

diethylamine

S-(9H-Xanthen-9-yl)cysteine

→

product

収率 78.0%

Nα-Trityl-S-(9H-xanthen-9-yl)-L-cysteine

収率 78.0%

溶媒

chloroform

反応条件

後処理

1. 1
   その他The reaction mixture was separated
2. 2
   洗浄The organic phase was washed twice with 4% diethylamine aqueous solution
3. 3
   乾燥The organic layer was dried over Na2SO4
4. 4
   その他The drying reagent was removed by filtration
5. 5
   その他condensed to dryness
6. 6
   その他by rotary evaporation
7. 7
   温度The residue was refluxed in 10 ml of a 1:30 mixture of diethyl amine/ethyl alcohol
8. 8
   その他The resultant diethyl ammonium salt was partitioned between 10 ml of ethyl acetate and 7 ml of 5% aqueous KHSO4 and 7 ml of water
9. 9
   その他The ethyl acetate layer was separated
10. 10
    乾燥was dried over MgSO4
11. 11
    濃縮was concentrated

実験手順

A sample of 1.0 g of S-(9H-Xanthen-9-yl)cysteine (3.3 mmole) from Example 4 was dissolved in 10 ml of chloroform. To the solution was added 1.5 ml of water and 1.5 ml of diethylamine. The mixture was cooled to 4° C. by an ice bath and 0.98 g of trityl chloride (3.5 mmole) was added in portions over a period of 30 min. After 2 h of stirring at room temperature. The reaction mixture was separated. The organic phase was washed twice with 4% diethylamine aqueous solution. The organic layer was dried over Na2SO4. The drying reagent was removed by filtration and the filtrate was condensed to dryness by rotary evaporation. The residue was refluxed in 10 ml of a 1:30 mixture of diethyl amine/ethyl alcohol. The resultant diethyl ammonium salt was partitioned between 10 ml of ethyl acetate and 7 ml of 5% aqueous KHSO4 and 7 ml of water. The ethyl acetate layer was separated and was dried over MgSO4 and was concentrated to get 1.4 g of product.

出典