Hydrochloric Acid → 7-[2-(2-Aminothiazol-4-yl)-2-(3-isoxazolylmethoxyimino)-acetamido]-3-cephem-4-carboxylic acid

HRID 894796Notes

Reaction equation

HRID 894796 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:25][O:26][CH2:27][C:28]2[CH:32]=[CH:31][O:30][N:29]=2)[C:10]([NH:12][CH:13]2[C:23](=[O:24])[N:15]3[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl>CO.O1CCCC1>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:25][O:26][CH2:27][C:28]2[CH:32]=[CH:31][O:30][N:29]=2)[C:10]([NH:12][CH:13]2[C:23](=[O:24])[N:15]3[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 1317123347-[2-(2-Formamidothiazol-4-yl)-2-(3-isoxazolylmethoxyimino)acetamido]-3-cephem-4-carboxylic acid

Product 1

HCID 1317123357-[2-(2-Aminothiazol-4-yl)-2-(3-isoxazolylmethoxyimino)-acetamido]-3-cephem-4-carboxylic acidYield 73.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-[2-(2-formamidothiazol-4-yl)-2-(3-isoxazolylmethoxyimino)acetamido]-3-cephem-4-carboxylic acid (syn isomer, 1.20 g.) and conc. hydrochloric acid (1.09 g.) in methanol (18 ml.) and tetrahydrofuran (9 ml.) was stirred at room temperature for 2 hours. The solution was treated in a similar manner to that of Example 5-(2) to give 7-[2-(2-aminothiazol-4-yl)-2-(3-isoxazolylmethoxyimino)-acetamido]-3-cephem-4-carboxylic acid (syn isomer, 0.83 g.).

Workup

  1. additionThe solution was treated in a similar manner to that of Example 5-(2)

Sources & evidence

ORD record
ord-9c0f57354ef7434da5d8e71160d9c308
Source dataset
uspto-grants-1981_08
Patent number
US04284631

Reaction notes

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