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

HRID 745417Notes

Reaction equation

HRID 745417 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 887MethanolSolvent2×HCID 8028TetrahydrofuranSolvent2×

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.) 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-94abffd4086640ad98bcf66b39c7ed0e
Source dataset
uspto-grants-1986_07
Patent number
US04598147

Reaction notes

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