Hydrochloric Acid → HCID 131714371, compound

HRID 464222Notes

Reaction equation

HRID 464222 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:33][O:34][CH3:35])[C:10]([NH:12][CH:13]2[C:31](=[O:32])[N:15]3[C:16]([C:28]([OH:30])=[O:29])=[C:17]([CH:20]=[CH:21][C:22]4[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl.C(OCC)(=O)C.C(=O)([O-])[O-].[K+].[K+]>CO.O1CCCC1.O>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:33][O:34][CH3:35])[C:10]([NH:12][CH:13]2[C:31](=[O:32])[N:15]3[C:16]([C:28]([OH:30])=[O:29])=[C:17]([CH:20]=[CH:21][C:22]4[CH:23]=[N:24][CH:25]=[CH:26][CH:27]=4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

8

Reactant 4

HCID 313Hydrochloric Acid2×HCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 131714372HCID 131714372, compound

Product 1

HCID 131714371HCID 131714371, compoundYield 39.7%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-[2-(3-pyridyl)vinyl]-3-cephem-4-carboxylic acid (syn isomer) (cis-trans mixture) (0.8 g) in methanol (6 ml), tetrahydrofuran (3 ml) and conc.hydrochloric acid (0.5 g) were stirred for 3 hours at ambient temperature. The resulting solution was added to a mixture of ethyl acetate and water and adjusted to pH 7.5 with 20% aqueous potassium carbonate. The separated aqueous layer was adjusted to pH 3.5 with 10% hydrochloric acid under ice-cooling. The precipitate was filtered off, washed with ice-water and dried over phosphorus pentoxide in vacuo to give 7-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[2-(3-pyridyl)vinyl]-3-cephem-4-carboxylic acid (syn isomer) (cis-trans mixture) (0.3 g).

Workup

  1. temperaturecooling
  2. filtrationThe precipitate was filtered off
  3. washwashed with ice-water
  4. dry with materialdried over phosphorus pentoxide in vacuo

Sources & evidence

ORD record
ord-5daefa509c3a4a6dbfad12a14aa4ad71
Source dataset
uspto-grants-1985_10
Patent number
US04546101

Reaction notes

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