반응 #1999

반응 방정식

benzyl alcohol

diphenylphosphoryl azide

2,2-dimethylbutanedioic acid-4-methyl ester

triethylamine

→

product

수율 75.1%

3-Benzyloxycarbonylamino-3-methylbutanoic acid, methyl ester

수율 75.1%

용매

benzene

반응 조건

후처리

1. 1
   온도The mixture was heated under nitrogen
2. 2
   온도at reflux for 45 minutes
3. 3
   온도refluxing
4. 4
   온도The mixture was cooled
5. 5
   여과filtered
6. 6
   농축the filtrate concentrated to a minimum volume under vacuum
7. 7
   workup.DISSOLUTIONThe residue was redissolved in 250 mL of ethyl acetate
8. 8
   세척washed with water, saturated aqueous sodium bicarbonate (2×) and brine
9. 9
   기타The organic layer was removed
10. 10
    건조dried over magnesium sulfate
11. 11
    여과filtered
12. 12
    농축the filtrate concentrated to a minimum volume under vacuum
13. 13
    기타The crude product was purified by medium pressure liquid chromatography on silica
14. 14
    세척eluting with hexane/ethyl acetate (4:1)

실험 절차

To 14.7 g (91.8 mmol) of 2,2-dimethylbutanedioic acid-4-methyl ester in 150 mL of benzene was added 13 mL of triethylamine (9.4 g, 93 mmol) followed by 21.8 mL of diphenylphosphoryl azide (27.8 g, 101 mmol). The mixture was heated under nitrogen at reflux for 45 minutes then 19 mL (19.9 g, 184 mmol) of benzyl alcohol was added and refluxing continued for 16 hours. The mixture was cooled, filtered and the filtrate concentrated to a minimum volume under vacuum. The residue was redissolved in 250 mL of ethyl acetate, washed with water, saturated aqueous sodium bicarbonate (2×) and brine. The organic layer was removed, dried over magnesium sulfate, filtered and the filtrate concentrated to a minimum volume under vacuum. The crude product was purified by medium pressure liquid chromatography on silica, eluting with hexane/ethyl acetate (4:1), to afford 18.27 g (68.9 mmol, 75%) of the product.

출처