Sodium Carbonate → 4-Nitrobenzyl-(4-allylthio-3-ethylazetidin-2-on-1-yl) acetate

HRID 1632262노트

반응식

HRID 1632262 반응식
[CH2:1]([S:4][CH:5]1[N:8](CC(O)=O)[C:7](=[O:13])[CH:6]1[CH2:14][CH3:15])[CH:2]=[CH2:3].[C:16](=[O:19])([O-])[O-:17].[Na+].[Na+].[N+:22]([C:25]1[CH:32]=[CH:31][C:28]([CH2:29]Br)=[CH:27][CH:26]=1)([O-:24])=[O:23].[CH3:33]C(N(C)C)=O>>[C:16]([O:17][N:8]1[CH:5]([S:4][CH2:1][CH:2]=[CH2:3])[C:6]([CH2:29][C:28]2[CH:31]=[CH:32][C:25]([N+:22]([O-:24])=[O:23])=[CH:26][CH:27]=2)([CH2:14][CH3:15])[C:7]1=[O:13])(=[O:19])[CH3:33]

참가 물질

5

반응물 4

HCID 10340Sodium CarbonateHCID 31374DimethylacetamideHCID 660114-Nitrobenzyl bromideHCID 13106496(4-Allylthio-3-ethylazetidin-2-on-1-yl)acetic acid

생성물 1

HCID 540931574-Nitrobenzyl-(4-allylthio-3-ethylazetidin-2-on-1-yl) acetate

실험 절차

To a solution of 2.5 g of (4-allylthio-3-ethylazetidin-2-on-1-yl)acetic acid in 8 ml of dimethylacetamide was added 0.636 g of freshly ground sodium carbonate. After stirring for 20 minutes, 2.591 g of 4-nitrobenzyl bromide were added in one batch. After about 45 minutes, when the starting material had been consumed, the solution was poured into water and extracted three times with ethyl acetate. The combined organic extracts were washed with saturated sodium bicarbonate, water and saturated brine, and then dried over magnesium sulphate, evaporated in vacuo and chromatographed on silica gel, eluting with ethyl acetate/hexane mixtures to give the title compound as a pale yellow oil. (Yield 3.08 g)

후처리

  1. waitAfter about 45 minutes
  2. customwhen the starting material had been consumed
  3. additionthe solution was poured into water
  4. extractionextracted three times with ethyl acetate
  5. washThe combined organic extracts were washed with saturated sodium bicarbonate, water and saturated brine
  6. dry with materialdried over magnesium sulphate
  7. customevaporated in vacuo
  8. customchromatographed on silica gel
  9. washeluting with ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-180419c568d742588b9ff590192f686d
출처 데이터셋
uspto-grants-1984_10
특허 번호
US04474793

반응 노트

불러오는 중…