Water → p-Nitrobenzyl 2-(4-Ethylthio-2-oxo-1-azetidinyl)-2-(ethoxythiocarbonylthio)acetate

HRID 2291000

반응식

HRID 2291000 반응식
[O:1]([CH2:5][CH3:6])[C:2]([S-:4])=[S:3].[K+].O.[CH2:9]([S:11][CH:12]1[N:15]([CH:16](Cl)[C:17]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=2)=[O:18])[C:14](=[O:31])[CH2:13]1)[CH3:10]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCl>[CH2:9]([S:11][CH:12]1[N:15]([CH:16]([S:3][C:2]([O:1][CH2:5][CH3:6])=[S:4])[C:17]([O:19][CH2:20][C:21]2[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=2)=[O:18])[C:14](=[O:31])[CH2:13]1)[CH3:10]

참가 물질

6

반응물 3

HCID 962WaterHCID 2735045Potassium ethylxanthateHCID 14050378p-Nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-chloroacetate

생성물 1

HCID 54336749p-Nitrobenzyl 2-(4-Ethylthio-2-oxo-1-azetidinyl)-2-(ethoxythiocarbonylthio)acetate

시약·촉매·용매 2

HCID 66133Benzyl triethylammonium chloride촉매HCID 6344Dichloromethane용매2회

실험 절차

To a stirred mixture of 3.2 g. of potassium ethyl xanthate, 5.4 g. of benzyltriethylammonium chloride, 100 ml. of water and 50 ml. of dichloromethane, at 0° C., was added a solution of 7.12 g. of p-nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-chloroacetate in 75 ml. of dichloromethane. Stirring was continued at 0°-5° C. for 1 hour, and then the organic phase was removed. The aqueous phase was extracted with 100 ml. of dichloromethane, and then the combined dichloromethane layers were washed successively with 75 ml. of dilute hydrochloric acid, 75 ml. of saturated aqueous sodium bicarbonate and 75 ml. of water. The dichloromethane solution was dried with anhydrous sodium sulfate and evaporated to dryness in vacuo, and the residue was purified by column chromatography on 200 g. of silica gel, eluting with 95:5 chloroform-ethyl acetate. The product containing fractions were combined and concentrated in vacuo to give 4.3 g of the title compound. The IR spectrum (chloroform) showed an absorption at 5.66 microns. The NMR spectrum (deuterochloroform) showed peaks at 1.02-1.6 (m, 6H); 2.35-3.65 (m, 4H); 4.4-5.1 (m, 3H); 5.3 (s, 2H); 6.3 and 6.4 (ss, 1H); 7.4 (d, 2H); and 8.2 (d, 2H) ppm.

후처리

  1. additionTo a stirred mixture of 3.2 g
  2. customthe organic phase was removed
  3. extractionThe aqueous phase was extracted with 100 ml
  4. washof dichloromethane, and then the combined dichloromethane layers were washed successively with 75 ml
  5. dry with materialThe dichloromethane solution was dried with anhydrous sodium sulfate
  6. customevaporated to dryness in vacuo
  7. customthe residue was purified by column chromatography on 200 g
  8. washof silica gel, eluting with 95:5 chloroform-ethyl acetate
  9. additionThe product containing fractions
  10. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-4dba25f2e84d4c5eb4aea2ab6f0bc5ab
출처 데이터셋
uspto-grants-1986_10
특허 번호
US04619783

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