Sodium Bicarbonate → 7-[2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid

HRID 1164573Notes

Reaction equation

HRID 1164573 reaction equation
Cl.[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8](=O)[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])[N:7]=1.C(=O)(O)[O-].[Na+].C([O-])(=O)C.[Na+].Cl.[O:36]([NH2:38])[CH3:37]>O>[NH2:2][C:3]1[S:4][CH:5]=[C:6]([C:8](=[N:38][O:36][CH3:37])[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])[N:7]=1

Participants

6

Reactant 4

HCID 516892Sodium Bicarbonate2×HCID 517045Sodium AcetateHCID 521874O-Methylhydroxylamine hydrochlorideHCID 88738031HCID 88738031, compound

Product 1

HCID 1317124447-[2-(2-Amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acidYield 6.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A solution of 7-[2-(2-amino-4-thiazolyl)glyoxyloylamino]-3-cephem-4-carboxylic acid hydrochloride (1.78 g) in water (100 ml) was adjusted to pH 6.0 with sodium bicarbonate under ice-cooling with stirring. Sodium acetate (0.38 g) and methoxylamine hydrochloride (1.37 g) were added to the solution adjusted to pH 7.0 with sodium bicarbonate and then stirred at 48° C. for an hour. The resultant solution was washed with ethyl acetate (200 ml) and diethyl ether (100 ml) in turn, and then nitrogen gas was bubbled into the solution to remove diethyl ether. The aqueous solution was adjusted to pH 3.5 with 10% hydrochloric acid under ice-cooling with stirring. The precipitates were collected by filtration, washed with water and dried over phosphorus pentoxide under reduced pressure to give 7-[2-(2-amino-4-thiazolyl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylic acid (syn isomer, 120 mg). The mother liquor was subjected to column chromatography on macroporous, nonionic adsorption resin "Diaion HP-20" (Trademark: manufactured by Mitsubishi Chemical Industries Ltd.) and eluted with 40% aqueous acetone. The eluate was concentrated under reduced pressure, lyophilized, and then dried over phosphorus pentoxide to give the same object compound (950 mg). Total yield 1070 mg.

Workup

  1. temperaturecooling
  2. stirringstirred at 48° C. for an hour
  3. washThe resultant solution was washed with ethyl acetate (200 ml) and diethyl ether (100 ml) in turn
  4. customnitrogen gas was bubbled into the solution
  5. customto remove diethyl ether
  6. temperaturecooling
  7. stirringwith stirring
  8. filtrationThe precipitates were collected by filtration
  9. washwashed with water
  10. dry with materialdried over phosphorus pentoxide under reduced pressure

Sources & evidence

ORD record
ord-b92959ff55f54a65be1e01ecf2b1d63e
Source dataset
uspto-grants-1983_01
Patent number
US04370326

Reaction notes

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