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

HRID 2296167Notes

Reaction equation

HRID 2296167 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 powder (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 of isopropyl alcohol. The eluate was adjusted to pH 3.5 with 10% hydrochloric acid under ice cooling, and the precipitates 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 powder (10 g.)
  6. filtrationthe precipitates were collected by filtration
  7. washwashed with water
  8. customdried

Sources & evidence

ORD record
ord-490aee0f44d94b3eb74052fe709e3d58
Source dataset
uspto-grants-1984_01
Patent number
US04427674

Reaction notes

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