Hydrochloric Acid → HCID 131713031, compound

HRID 1074943Notes

Reaction equation

HRID 1074943 reaction equation
[CH:1]1([O:6][N:7]=[C:8]([C:24]2[N:25]=[C:26]([NH:29]C=O)[S:27][CH:28]=2)[C:9]([NH:11][CH:12]2[C:22](=[O:23])[N:14]3[C:15]([C:19]([OH:21])=[O:20])=[CH:16][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:24]2[N:25]=[C:26]([NH2:29])[S:27][CH:28]=2)[C:9]([NH:11][CH:12]2[C:22](=[O:23])[N:14]3[C:15]([C:19]([OH:21])=[O:20])=[CH:16][CH2:17][S:18][C@H:13]23)=[O:10])[CH2:5][CH2:4][CH:3]=[CH:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 887MethanolHCID 131713032HCID 131713032, compound

Product 1

HCID 131713031HCID 131713031, compoundYield 86.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-[2-(2-cyclopenten-1-yl)oxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer) (1.6 g), conc.hydrochloric acid (1.1 g), methanol (20 ml) and tetrahydrofuran (15 ml) was stirred for 2 hours at room temperature. The reaction mixture was evaporated. The residue was dissolved in an aqueous solution of sodium bicarbonate and the solution was adjusted to pH 3.0 with hydrochloric acid. The precipitates were collected by filtration, washed with water and dried over phosphorus pentoxide to give 7-[2-(2-cyclopenten-1-yl)oxyimino-2-(2-aminothiazol-4-yl)acetamido]-3-cephem-4-carboxylic acid (syn isomer) (1.3 g). mp. 201° to 213° C. (dec.).

Workup

  1. customThe reaction mixture was evaporated
  2. dissolutionThe residue was dissolved in an aqueous solution of sodium bicarbonate
  3. filtrationThe precipitates were collected by filtration
  4. washwashed with water
  5. dry with materialdried over phosphorus pentoxide

Sources & evidence

ORD record
ord-df01801b3b654a188688b9dca2597600
Source dataset
uspto-grants-1983_07
Patent number
US04394384

Reaction notes

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