反应 #1999

反应方程式

benzyl alcohol

diphenylphosphoryl azide

2,2-dimethylbutanedioic acid-4-methyl ester

triethylamine

→

product

收率 75.1%

3-Benzyloxycarbonylamino-3-methylbutanoic acid, methyl ester

收率 75.1%

溶剂

benzene

反应条件

后处理

1. 1
   温度The mixture was heated under nitrogen
2. 2
   温度at reflux for 45 minutes
3. 3
   温度refluxing
4. 4
   温度The mixture was cooled
5. 5
   过滤filtered
6. 6
   浓缩the filtrate concentrated to a minimum volume under vacuum
7. 7
   workup.DISSOLUTIONThe residue was redissolved in 250 mL of ethyl acetate
8. 8
   洗涤washed with water, saturated aqueous sodium bicarbonate (2×) and brine
9. 9
   其他The organic layer was removed
10. 10
    干燥dried over magnesium sulfate
11. 11
    过滤filtered
12. 12
    浓缩the filtrate concentrated to a minimum volume under vacuum
13. 13
    其他The crude product was purified by medium pressure liquid chromatography on silica
14. 14
    洗涤eluting with hexane/ethyl acetate (4:1)

实验过程

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.

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