2,6-Lutidine → p-Nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-chloroacetate

HRID 1982148

반응식

HRID 1982148 반응식
[CH2:1]([S:3][CH:4]1[N:7]([CH:8](O)[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:10])[C:6](=[O:23])[CH2:5]1)[CH3:2].CC1C=CC=C(C)N=1.S(Cl)([Cl:34])=O>O1CCCC1>[CH2:1]([S:3][CH:4]1[N:7]([CH:8]([Cl:34])[C:9]([O:11][CH2:12][C:13]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][CH:14]=2)=[O:10])[C:6](=[O:23])[CH2:5]1)[CH3:2]

참가 물질

5

반응물 3

HCID 79372,6-LutidineHCID 24386Thionyl ChlorideHCID 14050377p-Nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-hydroxyacetate

생성물 1

HCID 14050378p-Nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-chloroacetate

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

To a stirred solution of 6.8 g. of p-nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-hydroxyacetate in 200 ml. of tetrahydrofuran at 0°-5° C. was added 2.98 ml. of 2,6-dimethylpyridine. This was followed by dropwise addition of a solution of 1.73 ml. of thionyl chloride in 20 ml. of tetrahydrofuran, over a 5-minute period. Stirring was continued at 0°-5° C. for 15 minutes, and then the reaction mixture was filtered. The filtrate was evaporated to dryness in vacuo, and the residue was dissolved in 200 ml. of dichloromethane. The resulting solution was washed successively with dilute hydrochloric acid and water, and dried with anhydrous sodium sulfate. Evaporation in vacuo gave the title compound as a yellow, viscous liquid (yield: 7.12 g). The IR spectrum (CHCl3) of the product showed an absorption at 5.63 microns. The NMR spectrum (CDCl3) of the product showed absorptions at 1.3(t,3H); 2.47-3.7(m,4H); 4.9-5.3(m, 1H); 5.4(s,4H); 6.06 and 6.18(ss,1H); 7.58 (d,2H); and 8.22(d,2H) ppm.

후처리

  1. additionThis was followed by dropwise addition of a solution of 1.73 ml
  2. filtrationthe reaction mixture was filtered
  3. customThe filtrate was evaporated to dryness in vacuo
  4. dissolutionthe residue was dissolved in 200 ml
  5. washThe resulting solution was washed successively with dilute hydrochloric acid and water
  6. dry with materialdried with anhydrous sodium sulfate
  7. customEvaporation in vacuo

출처 및 근거

ORD 기록
ord-f85d09ea25f64a0d84ae2cf9c50939c0
출처 데이터셋
uspto-grants-1986_06
특허 번호
US04595539

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