Water → cis-4-Acetoxymethyl-3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-2-oxoazetidine

HRID 621025Notes

Reaction equation

HRID 621025 reaction equation
[C:1]([O:4][CH2:5][C@H:6]1[NH:9][C:8](=[O:10])[C@H:7]1[NH2:11])(=[O:3])[CH3:2].C(=O)([O-])O.[Na+].[Cl:17][CH2:18][C:19]([NH:21][C:22]1[S:23][CH:24]=[C:25]([C:27](=[N:31][O:32][CH3:33])[C:28](Cl)=[O:29])[N:26]=1)=[O:20].O>O1CCCC1>[C:1]([O:4][CH2:5][C@H:6]1[NH:9][C:8](=[O:10])[C@H:7]1[NH:11][C:28](=[O:29])[C:27]([C:25]1[N:26]=[C:22]([NH:21][C:19](=[O:20])[CH2:18][Cl:17])[S:23][CH:24]=1)=[N:31][O:32][CH3:33])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 516892Sodium BicarbonateHCID 538001502-(2-Chloroacetamido-4-thiazolyl)-2-methoxyiminoacetyl chlorideHCID 70390316cis-4-Acetoxymethyl-3-amino-2-oxoazetidine

Product 1

HCID 86740461cis-4-Acetoxymethyl-3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-2-oxoazetidine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Under ice-cooling and stirring, 12 ml of an aqueous solution containing 632 mg of cis-4-acetoxymethyl-3-amino-2-oxoazetidine and 1.122 g of sodium hydrogen carbonate is added to a suspension of 2.36 g of 2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetyl chloride (syn-isomer) in 20 ml of tetrahydrofuran. The mixture is stirred for 2 hours at room temperature and the solvent is then distilled off in vacuo to leave the residue, which solidifies. Water is added to the solidified residue, followed by filtration. The collected crystals are washed successively with an aqueous sodium hydrogen carbonate solution, water and ether and dried to give cis-4-acetoxymethyl-3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-2-oxoazetidine (syn-isomer), m.p. 180°-190° C. (dec.).

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 the residue, which
  5. filtrationfollowed by filtration
  6. washThe collected crystals are washed successively with an aqueous sodium hydrogen carbonate solution, water and ether
  7. customdried

Sources & evidence

ORD record
ord-85a167b3e2624eeeb6e9f6a82fa556db
Source dataset
uspto-grants-1989_04
Patent number
US04822790

Reaction notes

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