Methanol → 2-(2-Aminothiazol-4-yl)-2-(2-hydroxyethoxyimino)acetic acid

HRID 27272Notes

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH2:15][CH2:16][O:17]C(=O)C2C=CC=CC=2)[C:8]([O:10]CC)=[O:9])[N:6]=1.CO.O1CCCC1>[OH-].[Na+]>[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:7](=[N:13][O:14][CH2:15][CH2:16][OH:17])[C:8]([OH:10])=[O:9])[N:6]=1

Participants

Conditions

Temperature: 40 °C

Procedure

A solution of ethyl 2-(2-aminothiazol-4-yl)-2-(2-benzoyloxyethoxyimino)acetate (syn isomer, 8.5 g.) in a mixture of 1 N aqueous sodium hydroxide (35 ml.), methanol (40 ml.) and tetrahydrofuran (40 ml.) was stirred at 40° C. for 9 hrs. and at room temperature for 12 hrs. The reaction mixture was treated in a conventional manner to give 2-(2-aminothiazol-4-yl)-2-(2-hydroxyethoxyimino)acetic acid (syn isomer, 3.3 g.).

Workup

waitand at room temperature for 12 hrs
additionThe reaction mixture was treated in a conventional manner

Sources & evidence

ORD record: ord-89a603e0af304765bbd9342fc21211dd
Source dataset: uspto-grants-1980_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04220761

Reaction notes

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