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

HRID 255768Notes

Reaction equation

HRID 255768 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:26][O:27][CH2:28][CH2:29][O:30]C=O)[C:10]([NH:12][CH:13]2[C:24](=[O:25])[N:15]3[C:16]([C:21]([OH:23])=[O:22])=[C:17]([CH3:20])[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:26][O:27][CH2:28][CH2:29][OH:30])[C:10]([NH:12][CH:13]2[C:24](=[O:25])[N:15]3[C:16]([C:21]([OH:23])=[O:22])=[C:17]([CH3:20])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 1317152957-[2-(2-Formamidothiazol-4-yl)-2-(2-formyloxyethoxyimino)acetamido]-3-methyl-3-cephem-4-carboxylic acid

Product 1

HCID 1317152967-[2-(2-Aminothiazol-4-yl)-2-(2-hydroxyethoxyimino)acetamido]-3-methyl-3-cephem-4-carboxylic acidYield 45.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-[2-(2-formamidothiazol-4-yl)-2-(2-formyloxyethoxyimino)acetamido]-3-methyl-3-cephem-4-carboxylic acid (syn isomer, 2.0 g.), conc. hydrochloric acid (1.35 g.), methanol (20 ml.) and tetrahydrofuran (20 ml.) was stirred at room temperature for 6 hours. After evaporating the reaction mixture in vacuo, the residue was subjected to column chromatography on non-ionic adsoption resin "Diaion HP-20" (trademark, manufactured by Mitsubishi Chemical Industries Ltd.) and eluted with 20% isopropyl alcohol. The eluate was concentrated in vacuo to give 7-[2-(2-aminothiazol-4-yl)-2-(2-hydroxyethoxyimino)acetamido]-3-methyl-3-cephem-4-carboxylic acid (syn isomer, 0.8 g.).

Workup

  1. customAfter evaporating the reaction mixture in vacuo
  2. wash" (trademark, manufactured by Mitsubishi Chemical Industries Ltd.) and eluted with 20% isopropyl alcohol
  3. concentrationThe eluate was concentrated in vacuo

Sources & evidence

ORD record
ord-779f129e7f8c4a0196673c026d7ff085
Source dataset
uspto-grants-1987_10
Patent number
US04698337

Reaction notes

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