Potassium Carbonate → HCID 131717752, compound

HRID 2082027Notes

Reaction equation

HRID 2082027 reaction equation
Cl.[NH2:2][C@@H:3]1[C:23](=[O:24])[N:5]2[C:6]([C:20]([O-:22])=[O:21])=[C:7]([CH2:10][N+:11]3[N:12]([CH2:17][CH2:18][OH:19])[C:13]([NH2:16])=[CH:14][CH:15]=3)[CH2:8][S:9][C@H:4]12.C(=O)(O)[O-].[Na+].[NH2:30][C:31]1[S:32][CH:33]=[C:34]([C:36](=[N:40][O:41][CH2:42][CH3:43])[C:37](O)=[O:38])[N:35]=1.ON1C2C=CC=CC=2N=N1.C(=O)([O-])[O-].[K+].[K+]>O.O1CCCC1.C(OCC)(=O)C>[NH2:30][C:31]1[S:32][CH:33]=[C:34]([C:36](=[N:40][O:41][CH2:42][CH3:43])[C:37]([NH:2][C@@H:3]2[C:23](=[O:24])[N:5]3[C:6]([C:20]([O-:22])=[O:21])=[C:7]([CH2:10][N+:11]4[N:12]([CH2:17][CH2:18][OH:19])[C:13]([NH2:16])=[CH:14][CH:15]=4)[CH2:8][S:9][C@H:4]23)=[O:38])[N:35]=1

Participants

9

Reactant 5

HCID 11430Potassium CarbonateHCID 757711-HydroxybenzotriazoleHCID 516892Sodium BicarbonateHCID 534242352-(2-Amino-4-thiazolyl)-2-ethoxyiminoacetic acidHCID 118856010HCID 118856010, compound

Product 1

HCID 131717752HCID 131717752, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
30 °C

Procedure

A solution of 7β-amino-3-[3-amino-2-(2-hydroxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate hydrochloride. dihydrate (1.5 g) in a mixture of water (15 ml) and tetrahydrofuran (30 ml) was adjusted to pH 7 with saturated sodium bicarbonate aqueous solution and 2-(2-aminothiazol-4-yl)-2-ethoxyiminoacetic acid (syn isomer) activated by 1-hydroxy-1H-benzotriazole (2.22 g) was added thereto at room temperature. The mixture was stirred for 5 hours at 30° C. maintaining pH 7 with addition of 20% potassium carbonate aqueous solution. To the reaction mixture was added ethyl acetate (30 ml) and the separated aqueous layer was washed with ethyl acetate (20 ml×2). The aqueous solution was adjusted to pH 4 with 1N-hydrochloric acid and washed with ethyl acetate (20 ml×3). The aqueous solution was adjusted to pH 2 with addition of 1N hydrochloric acid and subjected to column chromatography on "Diaion HP-20" (60 ml) using aqueous isopropyl alcohol, as an eluent. Fractions containing the object compound were combined and evaporated and lyophilized to give 7β-[2-(2-aminothiazol-4-yl)-2-ethoxyiminoacetamido ]-3-[3-amino-2-(2-hydroxyethyl)-1-pyrazolio]methyl-3-cephem-4-carboxylate (syn isomer) (1.30 g).

Workup

  1. additionwas added
  2. customat room temperature
  3. temperaturemaintaining pH 7
  4. washthe separated aqueous layer was washed with ethyl acetate (20 ml×2)
  5. washwashed with ethyl acetate (20 ml×3)
  6. additionThe aqueous solution was adjusted to pH 2 with addition of 1N hydrochloric acid
  7. additionFractions containing the object compound
  8. customevaporated

Sources & evidence

ORD record
ord-aadab69a032045dbbc141c8311fdc25a
Source dataset
uspto-grants-1993_02
Patent number
US05187160

Reaction notes

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