Dichloromethane → 3-Cephem

HRID 26113

반응식

HRID 26113 반응식
[N+](C1C=CC(COC(=O)/[C:11](/[N:22]2[CH:25]([S:26]S(C3C=CC(C)=CC=3)(=O)=O)[CH:24](NC(=O)COC3C=CC=CC=3)[C:23]2=[O:48])=[C:12](\OCC2C=CC=CC=2)/[CH3:13])=CC=1)([O-])=O.[N+](C1C=CC(COC(=O)/C=C\C)=CC=1)([O-])=O.N12CCCCC1C=NCCC2.C(Cl)Cl>O1CCCC1>[S:26]1[C@@H:25]2[CH2:24][C:23](=[O:48])[N:22]2[CH:11]=[CH:12][CH2:13]1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 705584062-[4-(p-Toluenesulphonylthio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-benzoxy-crotonic acid p-nitrobenzyl esterHCID 131711477Isocrotonic acid p-nitrobenzyl ester

생성물 1

HCID 208364673-Cephem

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of 731 mg (1 mmol) of a 1:1 mixture consisting of 2-[4-(p-toluenesulphonylthio)-3-phenoxyacetamido-2-oxoazetidin-1-yl]-3-benzoxy-crotonic acid p-nitrobenzyl ester and the corresponding isocrotonic acid p-nitrobenzyl ester in a mixture of 0.185 ml (1.2 mmols) of 1,5-diazabicyclo[5.4.0] undec-5-ene in 20 ml of dry tetrahydrofurane is stirred for precisely 35 minutes at room temperature. 50 ml of methylene chloride are added to the mixture and the whole is washed successively with dilute hydrochloric acid, water and dilute aqueous sodium bicarbonate solution. The organic phase is dried over sodium sulphate and concentrated by evaporation in vacuo. The residue is chromatographed on 25 mg of acid-washed silica gel, using toluene/ethyl acetate (3:1). A mixture consisting of the ceph-2-em compound and the ceph-3-em compound in the ratio of about 3:1 is obtained; this mixture can be separated by repeated chromatography into the pure isomers, giving 7β-phenoxyacetamido-3-benzoxy-ceph-2-em-4α-carboxylic acid p-nitrobenzyl ester of melting point 160° C.-162° C. (diethyl ether/pentane); IR spectrum (methylene chloride): characteristic bands at 5.6, 5.7, 5.9 and 7.4 μ, and 7β-phenoxyacetamido-3-benzoxy-ceph-3-em-4-carboxylic acid p-nitrobenzyl ester in the form of a colourless foam, IR spectrum (methylene chloride): characteristic bands at 5.6, 5.8 sh, 5.9, 7.9 and 8.4 μ.

후처리

  1. washthe whole is washed successively with dilute hydrochloric acid, water and dilute aqueous sodium bicarbonate solution
  2. dry with materialThe organic phase is dried over sodium sulphate
  3. concentrationconcentrated by evaporation in vacuo
  4. customThe residue is chromatographed on 25 mg of acid-washed silica gel

출처 및 근거

ORD 기록
ord-292769797baf47df9dbeb41346eb2640
출처 데이터셋
uspto-grants-1979_04
특허 번호
US04147864

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