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

HRID 256445Notes

Reaction equation

C([NH:3][C:4]1[S:5][C:6]([Br:38])=[C:7]([C:9](=[N:35][O:36][CH3:37])[C:10]([NH:12][CH:13]2[C:33](=[O:34])[N:15]3[C:16]([C:30]([OH:32])=[O:31])=[C:17]([CH2:20][O:21][C:22](=[O:29])[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.[ClH:39]>>[ClH:39].[NH2:3][C:4]1[S:5][C:6]([Br:38])=[C:7]([C:9](=[N:35][O:36][CH3:37])[C:10]([NH:12][CH:13]2[C:33](=[O:34])[N:15]3[C:16]([C:30]([OH:32])=[O:31])=[C:17]([CH2:20][O:21][C:22](=[O:29])[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

Reactant 2

HCID 313Hydrochloric Acid

HCID 1317153567-[2-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-benzoyloxymethyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317153577-[2-(2-Amino-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-benzoyloxymethyl-3-cephem-4-carboxylic acid hydrochloride

Procedure

7-[2-(2-Formamido-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-benzoyloxymethyl-3-cephem-4-carboxylic acid (syn isomer, 0.58 g.) was treated with conc. hydrochloric acid (0.16 ml.) in a similar manner to that of Example 1-(2) to give 7-[2-(2-amino-5-bromothiazol-4-yl)-2-methoxyiminoacetamido]-3-benzoyloxymethyl-3-cephem-4-carboxylic acid hydrochloride (syn isomer, 0.5 g.).

Sources & evidence

ORD record: ord-97b198a6b74d4bbe9abfcaf6a673a241
Source dataset: uspto-grants-1987_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04703046

Reaction notes

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