Pyridine → cis-3-[2-(2-Chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-4-chloroacetoxymethyl-2-oxoazetidine

HRID 621059노트

반응식

HRID 621059 반응식
[Cl:1][CH2:2][C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:22][O:23][CH3:24])[C:12]([NH:14][C@H:15]2[C@@H:18]([CH2:19][OH:20])[NH:17][C:16]2=[O:21])=[O:13])[N:10]=1)=[O:4].N1C=CC=CC=1.[Cl:31][CH2:32][C:33](Cl)=[O:34]>C(Cl)Cl.CN(C)C=O>[Cl:1][CH2:2][C:3]([NH:5][C:6]1[S:7][CH:8]=[C:9]([C:11](=[N:22][O:23][CH3:24])[C:12]([NH:14][C@H:15]2[C@@H:18]([CH2:19][O:20][C:33](=[O:34])[CH2:32][Cl:31])[NH:17][C:16]2=[O:21])=[O:13])[N:10]=1)=[O:4]

참가 물질

6

반응물 3

HCID 1049PyridineHCID 6577Chloroacetyl chlorideHCID 86740477cis-3-[2-(2-Chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-4-hydroxymethyl-2-oxoazetidine

생성물 1

HCID 86741506cis-3-[2-(2-Chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-4-chloroacetoxymethyl-2-oxoazetidine

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

In a mixture of 17 ml of methylene chloride and 6 ml of N,N-dimethylformamide is dissolved 172 mg of cis-3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-4-hydroxymethyl-2-oxoazetidine (syn-isomer), followed by addition of 0.2 ml of pyridine. While the mixture is cooled with ice-sodium chloride mixture and stirred, 0.12 ml of chloroacetyl chloride is added dropwise. The mixture is stirred under cooling for 30 minutes and the solvent is distilled off. To the residue are added aqueous sodium chloride and ethyl acetate, and the mixture is shaken well. The organic layer is separated and washed with aqueous sodium chloride and dried over anhydrous sodium sulfate. The solvent is then distilled off and the residue is crystallized from ether. Recrystallization from chloroform-methanol gives colorless crystals of cis-3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-4-chloroacetoxymethyl-2-oxoazetidine (syn-isomer), m.p. 225°-227° C. (decomp.).

후처리

  1. stirringThe mixture is stirred
  2. temperatureunder cooling for 30 minutes
  3. distillationthe solvent is distilled off
  4. additionTo the residue are added aqueous sodium chloride and ethyl acetate
  5. stirringthe mixture is shaken well
  6. customThe organic layer is separated
  7. washwashed with aqueous sodium chloride
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationThe solvent is then distilled off
  10. customthe residue is crystallized from ether
  11. customRecrystallization from chloroform-methanol

출처 및 근거

ORD 기록
ord-5273e44745c94aa6baa33eb5a920233a
출처 데이터셋
uspto-grants-1989_04
특허 번호
US04822790

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