Реакция #536951

Уравнение реакции

NaN3

NaNO2

25

(S)-5-(2-(4-aminobenzoyloxy)ethoxy)-2-(9H-carbazol-9-yl)-5-oxopentanoic acid

HCl

→

(S)-5-(2-(4-azidobenzoyloxy)ethoxy)-2-(9H-carbazol-9-yl)-5-oxopentanoic acid

Выход 85.0%

Растворители

water

water

acetone

Условия реакции

Обработка

1. 1
   workup.WAITAfter 20 min of stiffing at 0° C.
2. 2
   workup.WAITThe reaction mixture was stiffed for additional 30 min
3. 3
   Экстракцияextracted with ethyl acetate (100 mL)
4. 4
   Промывкаwashed with water (30 mL) and brine (30 mL)
5. 5
   СушкаThe final organic layer was dried over anhydrous Na2SO4
6. 6
   Фильтрацияfiltrated
7. 7
   Концентрированиеconcentrated under reduced pressure

Методика

To a stirred solution of 25 (0.38 g, 0.83 mmol) in acetone (8 mL) was added 5% HCl (8 mL) at 0° C. and the solution was stiffed for 5 min NaNO2 (0.70 g, 1.0 mmol) in 1 mL water was added dropwise to the above solution causing an immediate color change from colorless to orange. After 20 min of stiffing at 0° C., NaN3 (0.107 g, 1.65 mmol) in 1 mL water was added dropwise to the reaction mixture causing an immediate color changed from orange to colorless to pale yellow. The reaction mixture was stiffed for additional 30 min and extracted with ethyl acetate (100 mL), washed with water (30 mL) and brine (30 mL). The final organic layer was dried over anhydrous Na2SO4, filtrated and concentrated under reduced pressure to obtain (S)-5-(2-(4-azidobenzoyloxy)ethoxy)-2-(9H-carbazol-9-yl)-5-oxopentanoic acid 26 (0.34 g, 85%) as an off white gummy solid.

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