Sodium Hydroxide → 2-Cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetic acid

HRID 1723578Notes

Reaction equation

HRID 1723578 reaction equation
[CH:1]1([O:4][N:5]=[C:6]([C:12]2[N:13]=[C:14]([NH:17][CH:18]=[O:19])[S:15][CH:16]=2)[C:7]([O:9]CC)=[O:8])[CH2:3][CH2:2]1.[OH-].[Na+]>CO>[CH:1]1([O:4][N:5]=[C:6]([C:12]2[N:13]=[C:14]([NH:17][CH:18]=[O:19])[S:15][CH:16]=2)[C:7]([OH:9])=[O:8])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 53945259Ethyl 2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetate

Product 1

HCID 540072742-Cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetic acidYield 78%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of ethyl 2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetate (syn isomer)(9.92 g) in methanol (99.2 ml) was dropwise added 2N aqueous solution of sodium hydroxide (122 ml) below 10° C. The mixture was stirred under ice-cooling for 4 hours. The mixture was poured into ice-water, washed with ethyl acetate, adjusted to pH 2 with 6N hydrochloric acid under ice-cooling, and extracted with ethyl acetate. The extract was washed with saturated aqueous solution of sodium chloride, dried over magnesium sulfate and concentrated in vacuo. The residue was triturated with petroleum ether to give 2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetic acid (syn isomer)(6.97 g).

Workup

  1. temperaturecooling for 4 hours
  2. washwashed with ethyl acetate
  3. temperaturecooling
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with saturated aqueous solution of sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated with petroleum ether

Sources & evidence

ORD record
ord-ae6f14dac229472586714551bc0616cf
Source dataset
uspto-grants-1989_08
Patent number
US04861769

Reaction notes

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