Sodium Azide → 3-Azido-4-oxo-pentanoic acid methyl ester

HRID 1597459

반응식

HRID 1597459 반응식
[CH3:1][O:2][C:3](=[O:10])[CH2:4][CH:5](Br)[C:6](=[O:8])[CH3:7].[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C=O)C.O>[CH3:1][O:2][C:3](=[O:10])[CH2:4][CH:5]([N:11]=[N+:12]=[N-:13])[C:6](=[O:8])[CH3:7]

참가 물질

5

반응물 2

HCID 33557Sodium AzideHCID 10104516Methyl 3-bromo-4-oxopentanoate

생성물 1

HCID 545663833-Azido-4-oxo-pentanoic acid methyl ester수율 58.6%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

To a solution of 2.23 g (10.67 mmol) of 3-bromo4-oxo-pentanoic acid methyl ester in 11 mL of DMF at 0° C. was added 690 mg (10.67 mmol) of sodium azide. After warming to RT over 2.5 h, the reaction was diluted with water and extracted with diethyl ether/hexane (1:1). The layers were separated, the organics dried (Na2SO4), and the solvent removed in vacuo. The residue was purified by silica gel chromatography using diethyl ether/hexane (gradient of 1:4 to 2:3) to give 1.07 g (58% yield ) of the title compound: low resolution MS (FAB) m/e 172 (MH+).

후처리

  1. extractionextracted with diethyl ether/hexane (1:1)
  2. customThe layers were separated
  3. dry with materialthe organics dried (Na2SO4)
  4. customthe solvent removed in vacuo
  5. customThe residue was purified by silica gel chromatography

출처 및 근거

ORD 기록
ord-cd3907783d144dc1a3249b8e780e97f9
출처 데이터셋
uspto-grants-2001_09
특허 번호
US06294580B1

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