Hydrochloric Acid → 7-[2-(2-cyclopenten-1-yl)oxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[1-(2-carboxy-2-hydroxyiminoethyl)-1H-tetrazole-5-yl]thiomethyl-3-cephem-4-carboxylic acid

HRID 2412582Notes

Reaction equation

HRID 2412582 reaction equation
[CH:1]1([O:6][N:7]=[C:8]([C:38]2[N:39]=[C:40]([NH:43]C=O)[S:41][CH:42]=2)[C:9]([NH:11][CH:12]2[C:36](=[O:37])[N:14]3[C:15]([C:33]([OH:35])=[O:34])=[C:16]([CH2:19][S:20][C:21]4[N:25]([CH2:26][C:27]([C:30]([OH:32])=[O:31])=[N:28][OH:29])[N:24]=[N:23][N:22]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[CH2:5][CH2:4][CH:3]=[CH:2]1.Cl>CO.O1CCCC1>[CH:1]1([O:6][N:7]=[C:8]([C:38]2[N:39]=[C:40]([NH2:43])[S:41][CH:42]=2)[C:9]([NH:11][CH:12]2[C:36](=[O:37])[N:14]3[C:15]([C:33]([OH:35])=[O:34])=[C:16]([CH2:19][S:20][C:21]4[N:25]([CH2:26][C:27]([C:30]([OH:32])=[O:31])=[N:28][OH:29])[N:24]=[N:23][N:22]=4)[CH2:17][S:18][C@H:13]23)=[O:10])[CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 131713247HCID 131713247, compound

Product 1

HCID 1317132467-[2-(2-cyclopenten-1-yl)oxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[1-(2-carboxy-2-hydroxyiminoethyl)-1H-tetrazole-5-yl]thiomethyl-3-cephem-4-carboxylic acid

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of 7-[2-(2-cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-[1-(2-carboxy-2-hydroxyiminoethyl)-1H-tetrazol-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer: in the 7-position) (1.1 g) and conc. hydrochloric acid (0.12 g) in methanol (10 ml) and tetrahydrofuran (2 ml) was stirred at room temperature for 2.5 hours. After removal of organic solvents under reduced pressure, the residue was dissolved in an aqueous solution of sodium bicarbonate and the solution was adjusted to pH 7.5. The aqueous solution was washed with ethyl acetate (15 ml) and then adjusted to pH 3.0 with 10% hydrochloric acid to give precipitates which were filtered and washed with water to give 7-[2-(2-cyclopenten-1-yl)oxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-[1-(2-carboxy-2-hydroxyiminoethyl)-1H-tetrazole-5-yl]thiomethyl-3-cephem-4-carboxylic acid (syn isomer: in the 7-position).

Workup

  1. customAfter removal of organic solvents under reduced pressure
  2. dissolutionthe residue was dissolved in an aqueous solution of sodium bicarbonate
  3. washThe aqueous solution was washed with ethyl acetate (15 ml)
  4. customto give
  5. customprecipitates which
  6. filtrationwere filtered
  7. washwashed with water

Sources & evidence

ORD record
ord-9f41217f248a4db5a6b33409d755e2de
Source dataset
uspto-grants-1985_01
Patent number
US04493834

Reaction notes

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