Hydrochloric Acid → 2-(2-Aminothiazol-4-yl)-2-(cyclopropyloxyimino)acetic acid

HRID 1723577Notes

Reaction equation

HRID 1723577 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH:15]2[CH2:17][CH2:16]2)[C:8]([O:10]CC)=[O:9])[N:6]=1.[OH-].[Na+].Cl>O1CCOCC1.C(O)C>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH:15]2[CH2:17][CH2:16]2)[C:8]([OH:10])=[O:9])[N:6]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 53863683Ethyl 2-(2-aminothiazol-4-yl)-2-cyclopropyloxyiminoacetate

Product 1

HCID 540627172-(2-Aminothiazol-4-yl)-2-(cyclopropyloxyimino)acetic acidYield 157.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
33 °C

Procedure

To a solution of ethyl 2-(2-aminothiazol-4-yl)-2-(cyclopropyloxyimino)acetate (syn isomer)(1.88 g) in 1,4-dioxane (16.7 ml) was added 1N sodium hydroxide (16.7 ml). The mixture was stirred for 1.5 hours at 33° C. After the mixture was cooled under ice-bath, 1N hydrochloric acid (16.7 ml) was added to the mixture. The mixture was concentrated in vacuo to give a residue. The residue was suspended in ethanol, concentrated in vacuo and triturated with ethyl acetate to give crude 2-(2-aminothiazol-4-yl)-2-(cyclopropyloxyimino)acetic acid (syn isomer)(2.63 g). This compound was used for Preparation 33 without further purification.

Workup

  1. temperatureAfter the mixture was cooled under ice-bath
  2. concentrationThe mixture was concentrated in vacuo
  3. customto give a residue
  4. concentrationconcentrated in vacuo
  5. customtriturated with ethyl acetate

Sources & evidence

ORD record
ord-37a1452ff0e74499a283eb202893866e
Source dataset
uspto-grants-1989_08
Patent number
US04861769

Reaction notes

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