반응 #1999254

반응 방정식

N,N,N′-triethylethylenediamine

(R)-4-benzyl-3-(5-benzyloxypentanoyl)oxazolidin-2-one

sodium hexamethyldisilazane

tert-butyl bromoacetate

→

title compound

tert-Butyl 3-((R)-4-benzyl-2-oxooxazolidin-3-carbonyl)-6-benzyloxyhexanoate

용매

tetrahydrofuran

tetrahydrofuran

hexane

water

반응 조건

후처리

1. 1
   기타to −40° C
2. 2
   기타to −36° C
3. 3
   기타The aqueous layer was removed
4. 4
   세척the organic layer was washed with aqueous 20 w/v % citric acid (660 mL×3), water (660 mL), saturated aqueous sodium bicarbonate (660 mL) and brine (660 mL)
5. 5
   건조dried over magnesium sulfate
6. 6
   여과The magnesium sulfate was filtered off
7. 7
   농축the filtrate was concentrated in vacuo

실험 절차

A solution of (R)-4-benzyl-3-(5-benzyloxypentanoyl)oxazolidin-2-one (132 g) in tetrahydrofuran (660 mL) was added dropwise to a mixture of sodium hexamethyldisilazane (1.9 M in tetrahydrofuran) (702 mL) and tetrahydrofuran (660 mL) at −78° C. The reaction temperature was rose to −40° C. To the mixture was added dropwise tert-butyl bromoacetate (85 mL) at −78° C. The reaction temperature was rose to −36° C. To the mixture was added dropwise N,N,N′-triethylethylenediamine (33 mL) at ice temperature. And then, to the mixture were added water (530 mL) and hexane (660 mL). The aqueous layer was removed, and the organic layer was washed with aqueous 20 w/v % citric acid (660 mL×3), water (660 mL), saturated aqueous sodium bicarbonate (660 mL) and brine (660 mL), then dried over magnesium sulfate. The magnesium sulfate was filtered off and the filtrate was concentrated in vacuo to give the title compound (196 g) as a crude product.

출처