Phosphoric Acid → Sodium 3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-3-methoxy-2-oxoazetidine-1-sulfonate

HRID 978823Notes

Reaction equation

HRID 978823 reaction equation
[NH2:1][C:2]1([O:11][CH3:12])[CH2:5][N:4]([S:6]([OH:9])(=[O:8])=[O:7])[C:3]1=[O:10].[Cl:13][CH2:14][C:15]([NH:17][C:18]1[S:19][CH:20]=[C:21]([C:23](=[N:27][O:28][CH3:29])[C:24](O)=[O:25])[N:22]=1)=[O:16].C(=O)([O-])O.[Na+:34].P(=O)(O)(O)O>O.O1CCCC1>[Cl:13][CH2:14][C:15]([NH:17][C:18]1[S:19][CH:20]=[C:21]([C:23](=[N:27][O:28][CH3:29])[C:24]([NH:1][C:2]2([O:11][CH3:12])[CH2:5][N:4]([S:6]([O-:9])(=[O:7])=[O:8])[C:3]2=[O:10])=[O:25])[N:22]=1)=[O:16].[Na+:34]

Participants

7

Reactant 4

HCID 1004Phosphoric AcidHCID 516892Sodium BicarbonateHCID 581157C8H8ClN3O4SHCID 130190973-Amino-3-methoxy-2-oxoazetidine-1-sulfonic acid

Product 1

HCID 86741497Sodium 3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-3-methoxy-2-oxoazetidine-1-sulfonate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

In 1 ml of water is dissolved 30 mg of the above 3-amino-3-methoxy-2-oxoazetidine-1-sulfonic acid, and to the solution are added a solution of 89 mg of the acid chloride prepared from 2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetic acid (syn-isomer) in 1 ml of tetrahydrofuran and 36 mg of sodium hydrogen carbonate in alternate portions with ice-cooling and stirring. The mixture is further stirred at room temperature for 20 minutes and adjusted to pH 5.8 with phosphoric acid. After removal of tetrahydrofuran under reduced pressure, the water layer is washed with ethyl acetate and purified by Amberlite XAD-II chromatography. The above procedure yields 28 mg of sodium 3-[2-(2-chloroacetamido-4-thiazolyl)-2-methoxyiminoacetamido]-3-methoxy-2-oxoazetidine-1-sulfonate (syn-isomer) which is the same compound as the one described in Example 9.

Workup

  1. temperaturecooling
  2. stirringThe mixture is further stirred at room temperature for 20 minutes
  3. customAfter removal of tetrahydrofuran under reduced pressure
  4. washthe water layer is washed with ethyl acetate
  5. custompurified by Amberlite XAD-II chromatography

Sources & evidence

ORD record
ord-a0cb1234f4da4fe38ed9b4e353d349f2
Source dataset
uspto-grants-1987_05
Patent number
US04665067

Reaction notes

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