Diisopropyl Ether → Ethyl 2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetate

HRID 1074337Notes

Reaction equation

[C:1](OC(=O)C)(=[O:3])C.[NH2:8][C:9]1[S:10][CH:11]=[C:12]([C:14](=[N:20][O:21][CH:22]2[CH2:24][CH2:23]2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[N:13]=1.C(OC(C)C)(C)C>C(O)=O>[CH:22]1([O:21][N:20]=[C:14]([C:12]2[N:13]=[C:9]([NH:8][CH:1]=[O:3])[S:10][CH:11]=2)[C:15]([O:17][CH2:18][CH3:19])=[O:16])[CH2:24][CH2:23]1

Participants

Conditions

Temperature: 45 °C

Procedure

A mixture of formic acid (13.1 ml) and acetic anhydride (32.6 ml) was warmed at 45° C. for 45 minutes. After the mixture was cooled until ambient temperature, ethyl 2-(2-aminothiazol-4-yl)-2-cyclopropyloxyiminoacetate (syn isomer)(22 g) was added thereto. The suspension was turned to a clear solution and soon a precipitate was appeared. To the suspension was added diisopropyl ether (50 ml) and the mixture was stirred at ambient temperature for additional an hour. The mixture was cooled in ice-bath and the precipitate was collected and washed with diisopropyl ether to give ethyl 2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetate (syn isomer)(20.5 g).

Workup

temperatureAfter the mixture was cooled until ambient temperature
temperatureThe mixture was cooled in ice-bath
customthe precipitate was collected
washwashed with diisopropyl ether

Sources & evidence

ORD record: ord-df7706b358424132939c04aca6267a37
Source dataset: uspto-grants-1990_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04973699

Reaction notes

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