Hydrochloric Acid → 7-[2-(2-Amino-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid hydrochloride

HRID 568847Notes

Reaction equation

C([NH:3][C:4]1[S:5][C:6]([Br:33])=[C:7]([C:9](=[N:30][O:31][CH3:32])[C:10]([NH:12][CH:13]2[C:28](=[O:29])[N:15]3[C:16]([C:25]([OH:27])=[O:26])=[C:17]([CH2:20][O:21][C:22](=[O:24])[NH2:23])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.[ClH:34]>>[ClH:34].[NH2:3][C:4]1[S:5][C:6]([Br:33])=[C:7]([C:9](=[N:30][O:31][CH3:32])[C:10]([NH:12][CH:13]2[C:28](=[O:29])[N:15]3[C:16]([C:25]([OH:27])=[O:26])=[C:17]([CH2:20][O:21][C:22](=[O:24])[NH2:23])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 1317153477-[2-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317153487-[2-(2-Amino-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid hydrochloride

Procedure

7-[2-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid (syn isomer, 0.9 g.) was treated with conc. hydrochloric acid (0.34 ml.) in a similar manner so that of Example 1-(2) to give 7-[2-(2-amino-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-carbamoyloxymethyl-3-cephem-4-carboxylic acid hydrochloride (syn isomer, 850 mg.).

Sources & evidence

ORD record: ord-197871377b1a4d7aa9481eb56a899ca9
Source dataset: uspto-grants-1988_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04729991

Reaction notes

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