Hydrochloric Acid → 7-[2-(2-Aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylic acid hydrochloride

HRID 1200124Notes

Reaction equation

C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:28][O:29][CH3:30])[C:10]([NH:12][CH:13]2[C:26](=[O:27])[N:15]3[C:16]([C:23]([OH:25])=[O:24])=[C:17]([CH2:20][O:21][CH3:22])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.[ClH:31]>CO.O1CCCC1.C(OC(C)C)(C)C>[ClH:31].[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:28][O:29][CH3:30])[C:10]([NH:12][CH:13]2[C:26](=[O:27])[N:15]3[C:16]([C:23]([OH:25])=[O:24])=[C:17]([CH2:20][O:21][CH3:22])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

Conditions

Temperature: 30 °C

Procedure

To a suspension of 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylic acid (syn isomer) (0.52 g) in a mixture of methanol (3 ml) and tetrahydrofuran (2 ml) was added conc. hydrochloric acid (0.18 g), and the mixture was stirred at 30° C. for 4 hours. After the reaction mixture was cooled and diluted with diisopropyl ether, the precipitated crystals were collected by filtration, washed with diisopropyl ether and then dried to give 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-methoxymethyl-3-cephem-4-carboxylic acid hydrochloride (syn isomer) (0.45 g).

Workup

temperatureAfter the reaction mixture was cooled
filtrationthe precipitated crystals were collected by filtration
washwashed with diisopropyl ether
customdried

Sources & evidence

ORD record: ord-35ce9b218c6c4525849a3d98d4107706
Source dataset: uspto-grants-1990_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04904652

Reaction notes

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