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

HRID 2291002

반응식

HRID 2291002 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, 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 then dried over anhydrous sodium sulfate. Evaporation in vacuo gave 7.12 g of the title compound as a yellow, viscous liquid. The IR spectrum chloroform of the product showed an absorption at 5.63 microns. The NMR spectrum deuterochloroform of the product showed peaks 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. filtrationthe reaction mixture was filtered
  2. customThe filtrate was evaporated to dryness in vacuo
  3. dissolutionthe residue was dissolved in 200 ml
  4. washThe resulting solution was washed successively with dilute hydrochloric acid and water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customEvaporation in vacuo

출처 및 근거

ORD 기록
ord-4094fd8c3b144bd0984760f509810317
출처 데이터셋
uspto-grants-1986_10
특허 번호
US04619783

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