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

HRID 2231596
Notes
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Reaction equation

HRID 2231596 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228
Dimethylformamide
Solvent
HCID 6344DichloromethaneSolvent

Procedure

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.).

Workup

  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

Sources & evidence

ORD record
ord-115c5ff617c54f2db9da0c66d06782c3
Source dataset
uspto-grants-1988_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04782147

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes