반응 #4520

반응 방정식

Trifluoroacetic acid

Boc-L-Ala-D-Glu-(OH)OBzl

palmitoyl-L-Ala-D-Glu(OH)OBzl

→

palmitoyl-L-Ala-D-Glu(OH)OBzl

palmitoyl-L-Ala-D-Glu(OSu)OBzl

반응 조건

후처리

1. 1
   농축concentrated in vacuo
2. 2
   세척washed with diisopropylether
3. 3
   workup.DISSOLUTIONThe oil was dissolved in a mixture of water (15 ml) and sodium bicarbonate
4. 4
   workup.ADDITIONwas added until the pH of the solution
5. 5
   workup.ADDITIONThe mixture of water (6 ml) and acetone (20 ml)
6. 6
   workup.ADDITIONwas added to the solution and palmitoyl chloride (2.20 g)
7. 7
   workup.ADDITIONwas added in one portion
8. 8
   workup.STIRRINGAfter stirring for 30 minutes at room temperature
9. 9
   농축the reaction mixture was concentrated
10. 10
    workup.ADDITIONTo the residue was added water (30 ml)
11. 11
    기타the precipitates was collected
12. 12
    기타dried
13. 13
    기타to give a crude product, which
14. 14
    기타was purified by column chromatography of Silicagel (90 g) with chloroform-methanol (30:1

실험 절차

Trifluoroacetic acid (15 ml) was added to Boc-L-Ala-D-Glu-(OH)OBzl (1)(3.26 g) and the mixture was stirred for 20 minutes at room temperature, concentrated in vacuo and washed with diisopropylether. The oil was dissolved in a mixture of water (15 ml) and sodium bicarbonate was added until the pH of the solution became 8-9. The mixture of water (6 ml) and acetone (20 ml) was added to the solution and palmitoyl chloride (2.20 g) was added in one portion. After stirring for 30 minutes at room temperature, the pH of the solution was adjusted to 3 with 1N-hydrochloric acid and the reaction mixture was concentrated. To the residue was added water (30 ml) and the precipitates was collected and dried to give a crude product, which was purified by column chromatography of Silicagel (90 g) with chloroform-methanol (30:1, v/v) as an eluent to give palmitoyl-L-Ala-D-Glu(OH)OBzl (2)(2.00 g). mp. 131°-132° C.

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