Sodium Hydroxide → HCID 54276252, compound

HRID 2166299Notes

Reaction equation

HRID 2166299 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:15][O:16][CH:17]([CH2:27][CH3:28])[CH2:18][NH:19][C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[C:10]([O:12]CC)=[O:11])[N:8]=1)=[O:2].[OH-].[Na+]>C(O)C>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:15][O:16][CH:17]([CH2:27][CH3:28])[CH2:18][NH:19][C:20]([O:22][C:23]([CH3:25])([CH3:24])[CH3:26])=[O:21])[C:10]([OH:12])=[O:11])[N:8]=1)=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 131716485HCID 131716485, compound

Product 1

HCID 54276252HCID 54276252, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

1.65 g of ethyl 2-(2-formamidothiazol-4-yl)-2-hydroxyiminoacetate (syn isomer) is dissolved in 30 ml of dimethylformamide. To this solution, 165 mg of sodium hydride is added, and this is followed by 10 minutes of agitation at room temperature. 2.5 g of the product obtained in (1) is then added, and this is followed by 15 hours of agitation at the same temperature. 200 ml of ethyl acetate is added, and this mixture is washed with 200 ml of a sodium chloride solution and dried with anhydrous Glauber's salt. The dried solution is concentrated under reduced pressure, subjected to silica gel column chromatography, and eluted with n-hexane-ethyl acetate, whereafter the desired fraciton is concentrated to give 1.3 g of ethyl 2-(2-formamidothiazol-4-yl)-2-(2-t-butoxycarbonylamino-1-ethylethoxyimino)acetate) (syn isomer). This ester is dissolved in 13 ml of ethanol. To this solution, 3.1 ml of an aqueous solution of 2N sodium hydroxide is added, and this is followed by 2 hours of agitation at room temperature. This mixture is concentrated under reduced pressure. To this concentrate, 200 ml of ethyl acetate is added, and this mixture is washed with 100 ml of 10% citric acid and 100 ml of a sodium chloride solution, and dried with anhydrous Glauber's salt. The dried solution is concentrated under reduced pressure to give 1.1 g of 2-(2-formamidothiazol-4-yl)-2-(2-t-butoxycarbonylamino-1-ethylethoxyimino)acetic acid (syn isomer).

Workup

  1. concentrationThis mixture is concentrated under reduced pressure
  2. additionTo this concentrate, 200 ml of ethyl acetate is added
  3. washthis mixture is washed with 100 ml of 10% citric acid and 100 ml of a sodium chloride solution
  4. dry with materialdried with anhydrous Glauber's salt
  5. concentrationThe dried solution is concentrated under reduced pressure

Sources & evidence

ORD record
ord-7a3e9f3cd6c74dbea9f2e03dedb234c7
Source dataset
uspto-grants-1990_07
Patent number
US04943567

Reaction notes

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