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

HRID 653283Notes

Reaction equation

HRID 653283 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-cooliing 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 (syn isomer) in 10 ml of tetrahydrofuran. After the mixture is stirred for 2 hours at room temperature, the solvent is distilled off in vacuo to leave a residue, which solidifies. Water is added to the solid, followed by filtration, and the collected crystals are washed successively with water and ethanol to give cis-3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-2-oxoazetidine-4-carboxylic acid methyl ester (syn isomer), m.p. 270°-275° C. (dec.). .

Workup

  1. stirringAfter the mixture is stirred for 2 hours at room temperature
  2. distillationthe solvent is distilled off in vacuo
  3. customto leave a residue, which
  4. filtrationfollowed by filtration
  5. washthe collected crystals are washed successively with water and ethanol

Sources & evidence

ORD record
ord-e753804896284046b10cc5c47a2838b6
Source dataset
uspto-grants-1987_06
Patent number
US04675397

Reaction notes

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