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

HRID 653313ノート

反応式

HRID 653313 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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 chlorform-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.).

後処理

  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 chlorform-methanol

出典と根拠

ORDレコード
ord-0778d5699abd4179bce25ecce8cdadb7
出典データセット
uspto-grants-1987_06
特許番号
US04675397

反応ノート

読み込み中…