Hydrochloric Acid → 7-[2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

HRID 1164264Notes

Reaction equation

[NH2:1][C:2]([NH2:4])=[S:3].C([O-])(=O)C.[Na+].[CH3:10][O:11][N:12]=[C:13]([C:29](=O)[CH:30](Br)Br)[C:14]([NH:16][CH:17]1[C:27](=[O:28])[N:19]2[C:20]([C:24]([OH:26])=[O:25])=[CH:21][CH2:22][S:23][C@H:18]12)=[O:15].Cl>O1CCCC1.O>[NH2:1][C:2]1[S:3][CH:30]=[C:29]([C:13](=[N:12][O:11][CH3:10])[C:14]([NH:16][CH:17]2[C:27](=[O:28])[N:19]3[C:20]([C:24]([OH:26])=[O:25])=[CH:21][CH2:22][S:23][C@H:18]23)=[O:15])[N:4]=1

Participants

Conditions

Temperature: 30 °C

Procedure

Thiourea (235 mg) and sodium acetate (253 mg) were added to a solution of 7-(2-methoxyimino-3-oxo-4,4-dibromobutyramido)-3-cephem-4-carboxylic acid (syn isomer, 500 mg) in tetrahydrofuran (10 ml) and water (100 ml), and the mixture was stirred at 30° C. for 4 hours. The resultant solution was adjusted to pH 3.5 with 6 N hydrochloric acid, and concentrated under reduced pressure. The precipitates were collected by filtration, washed with water and dried to give 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 163 mg).

Workup

concentrationconcentrated under reduced pressure
filtrationThe precipitates were collected by filtration
washwashed with water
customdried

Sources & evidence

ORD record: ord-57b4f7f6dea440e584a98183eec999a3
Source dataset: uspto-grants-1983_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04368325

Reaction notes

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