Methanol → 2-Isopropoxyimino-2-(2-aminothiazol-4-yl)acetic acid

HRID 1284677Notes

Reaction equation

HRID 1284677 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH:15]([CH3:17])[CH3:16])[C:8]([O:10]CC)=[O:9])[N:6]=1.[OH-].[Na+].CO>O1CCCC1>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH:15]([CH3:17])[CH3:16])[C:8]([OH:10])=[O:9])[N:6]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 54000557Ethyl 2-(2-amino-4-thiazolyl)-2-(1-methylethoxyimino)acetate

Product 1

HCID 541000552-Isopropoxyimino-2-(2-aminothiazol-4-yl)acetic acidYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 2-(2-aminothiazol-4-yl)-2-iso-propoxyiminoacetate (syn isomer, 26.8 g.), 1N aqueous solution of sodium hydroxide (156 ml.), methanol (156 ml.) and tetrahydrofuran (100 ml.) were treated in a similar manner to that of Example D-(4) to give 2-(2-aminothiazol-4-yl)-2-iso-propoxyiminoacetic acid (syn isomer, 15.3 g.), mp. 151° C. (dec.).

Sources & evidence

ORD record
ord-c044ae25a8834f8f9c9fdbdf218d6e73
Source dataset
uspto-grants-1986_01
Patent number
US04563522

Reaction notes

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