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

HRID 621299Notes

Reaction equation

HRID 621299 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:25][O:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:10]([NH:12][CH:13]2[C:23](=[O:24])[N:15]3[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl.CO.C(=O)(O)[O-].[Na+]>O.C(O)(C)C.O1CCCC1>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:25][O:26][CH2:27][CH2:28][CH2:29][CH3:30])[C:10]([NH:12][CH:13]2[C:23](=[O:24])[N:15]3[C:16]([C:20]([OH:22])=[O:21])=[CH:17][CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

8

Reactant 4

HCID 313Hydrochloric Acid3×HCID 887MethanolHCID 516892Sodium BicarbonateHCID 1317124577-[2-(2-Formamidothiazol-4-yl)-2-butoxyiminoacetamido]-3-cephem-4-carboxylic acid

Product 1

HCID 1317124587-[2-(2-Aminothiazol-4-yl)-2-n-butoxyiminoacetamido]-3-cephem-4-carboxylic acidYield 60.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-[2-(2-formamidothiazol-4-yl)-2-n-butoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 12.7 g.), conc. hydrochloric acid (9.6 ml.) methanol (9.5 ml.) and tetrahydrofuran (9.5 ml.) was stirred at room temperature for 3 hours. The resultant solution was concentrated in vacuo, and the residue was suspended in water. The suspension was adjusted to pH 3.5 with sodium bicarbonate under ice cooling, and stirred at same temperature for 30 minutes. The precipitates were collected by filtration and dried over magnesium sulfate to give the power (10 g.). The powder was suspended in water (300 ml.) and adjusted to pH 7.0 with sodium bicarbonate. The solution was adjusted to pH 6.0 with 10% hydrochloric acid and subjected to column chromatography on nonionic adsorption resin (Diaion HP-20: trademark, manufactured by Mitsubishi Chemical Industries Ltd.) (300 ml.) with 10% aqueous solution os isopropyl alcohol. The eluate was adjusted to pH 3.5 with 10% hydrochloric acid under ice cooling, and the precipiatates were collected by filtration, washed with water and dried to give 7-[2-(2-aminothiazol-4-yl)-2-n-butoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 7.2 g.).

Workup

  1. concentrationThe resultant solution was concentrated in vacuo
  2. stirringstirred at same temperature for 30 minutes
  3. filtrationThe precipitates were collected by filtration
  4. dry with materialdried over magnesium sulfate
  5. customto give the power (10 g.)
  6. filtrationthe precipiatates were collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-dc871d369e834166b7273b834e6b3ccb
Source dataset
uspto-grants-1989_04
Patent number
US04822888

Reaction notes

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