Reaktion #514568

Reaktionsgleichung

methyl iodide

Boc-Thr-OH

sodium hydride

→

title compound

Boc-Thr(Me)-OH

Lösungsmittel

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   workup.ADDITIONwas added under ice cooling
2. 2
   Sonstigethe obtained reaction mixture
3. 3
   SonstigeThe reaction mixture was evaporated under reduced pressure
4. 4
   workup.DISSOLUTIONthe resultant residue was redissolved in ethyl acetate
5. 5
   Waschenwashed with 5% sodium hydrogensulfite aqueous solution, water and saturated sodium chloride aqueous solution
6. 6
   Trocknensuccessively, and dried over anhydrous sodium sulfate
7. 7
   SonstigeThe dried solution was evaporated under reduced pressure
8. 8
   workup.DISSOLUTIONdissolved in methanol
9. 9
   workup.ADDITIONmixed with DCHA
10. 10
    Sonstigereevaporated
11. 11
    workup.ADDITIONEther-hexane was added to the residue

Vorschrift

In a THF solution containing 0.8 g of Boc-Thr-OH, 100 mg of sodium hydride (60% in oil) was added under ice cooling and the resultant mixture was stirred for 30 min at room temperature. Further, 2.8 ml of methyl iodide was added and the obtained reaction mixture was stirred overnight at room temperature. The reaction mixture was evaporated under reduced pressure and the resultant residue was redissolved in ethyl acetate, washed with 5% sodium hydrogensulfite aqueous solution, water and saturated sodium chloride aqueous solution, successively, and dried over anhydrous sodium sulfate. The dried solution was evaporated under reduced pressure, dissolved in methanol, mixed with DCHA and reevaporated. Ether-hexane was added to the residue to give 0.55 g of the title compound as its DCHA salt.

Quelle