Hydrochloric Acid → 7-[2-(2-Aminothiazol-4-yl)-2-n-propoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid

HRID 2295638Notes

Reaction equation

HRID 2295638 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:26][O:27][CH2:28][CH2:29][CH3:30])[C:10]([NH:12][CH:13]2[C:24](=[O:25])[N:15]3[C:16]([C:21]([OH:23])=[O:22])=[C:17]([Cl:20])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl>CO>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:26][O:27][CH2:28][CH2:29][CH3:30])[C:10]([NH:12][CH:13]2[C:24](=[O:25])[N:15]3[C:16]([C:21]([OH:23])=[O:22])=[C:17]([Cl:20])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 1317124687-[2-(2-Formamidothiazol-4-yl)-2-n-propoxyiminoacetamido)-3-chloro-3-cephem-4-carboxylic acid

Product 1

HCID 1317124697-[2-(2-Aminothiazol-4-yl)-2-n-propoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acidYield 42.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 7-[2-(2-formamidothiazol-4-yl)-2-n-propoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 1.5 g.), conc. hydrochloric acid (0.7 ml.) and methanol (30 ml.) was stirred at room temperature for 1.5 hours. After removing methanol from the resultant solution in vacuo, water (30 ml.) was added to the residue. After the solution was adjusted to pH 7.5 with a saturated aqueous solution of sodium bicarbonate, the insoluble substance was removed by filtration. The filtrate was adjusted to pH 3 with 10% hydrochloric acid. The precipitates were collected by filtration and dried over phosphorus pentoxide to give 7-[2-(2-aminothiazol-4-yl)-2-n-propoxyiminoacetamido]-3-chloro-3-cephem-4-carboxylic acid (syn isomer, 0.6 g.).

Workup

  1. customAfter removing methanol from the resultant solution in vacuo, water (30 ml.)
  2. additionwas added to the residue
  3. customthe insoluble substance was removed by filtration
  4. filtrationThe precipitates were collected by filtration
  5. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-745a6f114d1d43c5afc85edfaff564c4
Source dataset
uspto-grants-1984_01
Patent number
US04425341

Reaction notes

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