Reaktion #47740

Reaktionsgleichung

trityl chloride

water

diethylamine

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

→

product

Ausbeute 78.0%

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

Ausbeute 78.0%

Lösungsmittel

chloroform

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeThe reaction mixture was separated
2. 2
   WaschenThe organic phase was washed twice with 4% diethylamine aqueous solution
3. 3
   TrocknenThe organic layer was dried over Na2SO4
4. 4
   SonstigeThe drying reagent was removed by filtration
5. 5
   Sonstigecondensed to dryness
6. 6
   Sonstigeby rotary evaporation
7. 7
   TemperaturThe residue was refluxed in 10 ml of a 1:30 mixture of diethyl amine/ethyl alcohol
8. 8
   SonstigeThe 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
   SonstigeThe ethyl acetate layer was separated
10. 10
    Trocknenwas dried over MgSO4
11. 11
    Einengenwas concentrated

Vorschrift

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.

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