p-Nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-chloroacetate → p-Nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-[2-ethoxyethylthio(thiocarbonyl)thio]acetate

HRID 4436

반응식

HRID 4436 반응식
[C:1](=[S:9])([S-:8])[S:2][CH2:3][CH2:4][O:5][CH2:6][CH3:7].[K+].[CH2:11]([S:13][CH:14]1[N:17]([CH:18](Cl)[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[O:20])[C:16](=[O:33])[CH2:15]1)[CH3:12]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[CH2:11]([S:13][CH:14]1[N:17]([CH:18]([S:9][C:1]([S:2][CH2:3][CH2:4][O:5][CH2:6][CH3:7])=[S:8])[C:19]([O:21][CH2:22][C:23]2[CH:28]=[CH:27][C:26]([N+:29]([O-:31])=[O:30])=[CH:25][CH:24]=2)=[O:20])[C:16](=[O:33])[CH2:15]1)[CH3:12]

참가 물질

5

반응물 2

HCID 14050378p-Nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-chloroacetateHCID 23707565Potassium 2-ethoxyethyl trithiocarbonate

생성물 1

HCID 13686092p-Nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-[2-ethoxyethylthio(thiocarbonyl)thio]acetate수율 30.9%

시약·촉매·용매 2

HCID 66133Benzyl triethylammonium chloride촉매HCID 6344Dichloromethane용매2회

실험 절차

A solution of 3.58 g potassium 2-ethoxyethyl trithiocarbonate and 3.7 g benzyltriethylammonium chloride in 100 ml methylene chloride was cooled to 0° C. under a nitrogen atmosphere and a solution of 5.3 g of p-nitrobenzyl 2-(4-ethylthio-2-oxo-1-azetidinyl)-2-chloroacetate in 50 ml methylene chloride was added dropwise. The reaction mixture was stirred for 1 hour, then washed with three 50 ml portions of water, dried over anhydrous sodium sulfate and concentrated in vacuo to an oil. (8.6 g). The crude product was chromatographed on silica gel eluting with 5% ethyl acetate in chloroform to yield 2.3 g of the title compound as an oil. The IR spectrum of a chloroform solution of the title compound had an absorption at 5.65 micron; and the NMR spectrum in deuterochloroform showed peeks at 1.2(m, 6H); 2.34-3.77(c, 10H); 4.7,4.98(m, 1H); 5.26(s, 2H); 6.62, 6.86(s, 1H); 7.43(m, 2H); and 8.16(m, 2H). ppm.

후처리

  1. washwashed with three 50 ml portions of water
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo to an oil
  4. customThe crude product was chromatographed on silica gel eluting with 5% ethyl acetate in chloroform

출처 및 근거

ORD 기록
ord-5cd096596a2f40b4833d1c38618339f5
출처 데이터셋
uspto-grants-1988_02
특허 번호
US04725678

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