Methanol → 2-(2-Aminothiazol-4-yl)-2-propargyloxyiminoacetic acid

HRID 1154110Notes

Reaction equation

HRID 1154110 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH2:15][C:16]#[CH:17])[C:8]([O:10]CC)=[O:9])[N:6]=1.CO.[OH-].[Na+]>O1CCCC1>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH2:15][C:16]#[CH:17])[C:8]([OH:10])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 53907014Ethyl 2-(2-aminothiazol-4-yl)-2-propargyloxyiminoacetate

Product 1

HCID 543726822-(2-Aminothiazol-4-yl)-2-propargyloxyiminoacetic acidYield 77.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
30 °C

Procedure

A mixture of ethyl 2-(2-aminothiazol-4-yl)-2-propargyloxyiminoacetate (syn isomer, 2.8 g.), methanol (23 ml.), tetrahydrofuran (20 ml.) and 1N aqueous solution of sodium hydroxide (22.17 ml.) was stirred at 30° C. for 5 hrs. The reaction mixture was treated in a conventional manner to give 2-(2-aminothiazol-4-yl)-2-propargyloxyiminoacetic acid (syn isomer, 1.924 g.).

Workup

  1. additionThe reaction mixture was treated in a conventional manner

Sources & evidence

ORD record
ord-5f7b54ad02a74b3a8560848328188df2
Source dataset
uspto-grants-1984_12
Patent number
US04487767

Reaction notes

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