Water → cis-3-[2-(2-Chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-2-oxoazetidine-4-carboxylic acid methyl ester

HRID 978871Notes

Reaction equation

HRID 978871 reaction equation
[CH3:1][O:2][C:3]([C@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH2:10])=[O:4].C(=O)([O-])O.[Na+].[Cl:16][CH2:17][C:18]([NH:20][C:21]1[S:22][CH:23]=[C:24]([C:26](=[N:30][O:31][CH3:32])[C:27](Cl)=[O:28])[N:25]=1)=[O:19].O>O1CCCC1>[CH3:1][O:2][C:3]([C@H:5]1[NH:8][C:7](=[O:9])[C@H:6]1[NH:10][C:27](=[O:28])[C:26]([C:24]1[N:25]=[C:21]([NH:20][C:18](=[O:19])[CH2:17][Cl:16])[S:22][CH:23]=1)=[N:30][O:31][CH3:32])=[O:4]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 538001502-(2-Chloroacetamido-4-thiazolyl)-2-methoxyiminoacetyl chlorideHCID 53988551cis-3-Amino-4-methoxycarbonyl-2-oxoazetidine

Product 1

HCID 86740462cis-3-[2-(2-Chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-2-oxoazetidine-4-carboxylic acid methyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under ice-cooling and stirring, 6 ml of an aqueous solution containing 288 mg of cis-3-amino-2-oxoazetidine-4-carboxylic acid methyl ester and 561 mg of sodium hydrogen carbonate is added to a suspension of 1.18 g of 2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetyl chloride (anti isomer) in 10 ml of tetrahydrofuran. The mixture is stirred for 2 hours at room temperature and the solvent is then distilled off in vacuo to leave a residue, which solidifies. Water is added to the solidified residue, followed by filtration. The filtrate is neutralized with an aqueous sodium hydrogen carbonate solution and then extracted with chloroform. The chloroform layer is dried over anhydrous sodium sulfate and the solvent is distilled off in vacuo to give cis-3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-2-oxoazetidine-4-carboxylic acid methyl ester (anti-isomer). m.p. 119°-129° C.

Workup

  1. temperatureUnder ice-cooling
  2. stirringThe mixture is stirred for 2 hours at room temperature
  3. distillationthe solvent is then distilled off in vacuo
  4. customto leave a residue, which
  5. filtrationfollowed by filtration
  6. extractionextracted with chloroform
  7. dry with materialThe chloroform layer is dried over anhydrous sodium sulfate
  8. distillationthe solvent is distilled off in vacuo

Sources & evidence

ORD record
ord-0254463fc1634518968b0043d1afeb12
Source dataset
uspto-grants-1987_05
Patent number
US04665067

Reaction notes

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