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

HRID 848272Notes

Reaction equation

HRID 848272 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

Procedure

N.M.R. δ(DMSO-d6, ppm): 1.28 (3H, t, J=7 Hz), 3.49 (1H, t, J=3 Hz), 4.31 (2H, q, J=7 Hz), 4.76 (2H, d, J=3 Hz), 6.95 (1H, s), 7.29 (2H, s). p (4) Ethyl 2-(2-aminothiazol-4-yl)-2-propargyloxyiminoacetate (syn isomer, 2.8 g.), methanol (23 ml.), tetrahydrofuran (20 ml.) and 1 N aqueous solution of sodium hydroxide (22.17 ml.) were treated in a similar manner to that of Example F-(4) to give 2-(2-aminothiazol-4-yl)-2-propargyloxyiminoacetic acid (syn isomer, 1.924 g.).

Sources & evidence

ORD record
ord-6503cd5fa1394b53a118c1fa8f1b8edb
Source dataset
uspto-grants-1981_10
Patent number
US04294960

Reaction notes

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