Sodium Bicarbonate → HCID 131718946, compound

HRID 1734275Notes

Reaction equation

HRID 1734275 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7](=[N:31][O:32][CH2:33][C:34]([OH:36])=[O:35])[C:8]([NH:10][C@@H:11]2[C:29](=[O:30])[N:13]3[C:14]([C:26]([O-:28])=[O:27])=[C:15]([CH2:18][N+:19]4([CH3:25])[CH2:24][CH2:23][NH:22][CH2:21][CH2:20]4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1.C(=O)(O)[O-].[Na+].C([O:45][C:46]1[CH:47]=[C:48]([CH:52]=[CH:53][C:54]=1[O:55]C(=O)C)[C:49](Cl)=[O:50])(=O)C>CC(C)=O.O>[NH2:1][C:2]1[S:6][N:5]=[C:4]([C:7](=[N:31][O:32][CH2:33][C:34]([OH:36])=[O:35])[C:8]([NH:10][C@@H:11]2[C:29](=[O:30])[N:13]3[C:14]([C:26]([O-:28])=[O:27])=[C:15]([CH2:18][N+:19]4([CH3:25])[CH2:20][CH2:21][N:22]([C:49](=[O:50])[C:48]5[CH:52]=[CH:53][C:54]([OH:55])=[C:46]([OH:45])[CH:47]=5)[CH2:23][CH2:24]4)[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 140969484-(Chlorocarbonyl)-1,2-phenylene diacetateHCID 131718127HCID 131718127, compound

Product 1

HCID 131718946HCID 131718946, compoundYield 39.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

The solution of 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-(1-methyl-1-piperazinio)methyl-3-cephem-4-carboxylate (syn isomer) (540 mg) in acetone (5 ml) and water (5 ml) was adjusted to pH 7.0 with a saturated aqueous solution of sodium bicarbonate. To the mixture was added 3,4-diacetoxybenzoyl chloride (308 mg) at pH 6.5-7.0. The mixture was stirred for an hour and evaporated in vacuo to remove acetone. The residue was adjusted to pH 8.5 with a saturated aqueous solution of sodium bicarbonate and then stirred for 2 hours at room temperature. The mixture was adjusted to pH 3.5 with 3N hydrochloric acid and then filtered. The filtrate was subjected to column chromatography on Diaion HP-20 using 5% aqueous isopropyl alcohol as an eluent. The eluate was evaporated in vacuo to remove isopropyl alcohol and then lyophilized to give 7β-[2-(5-amino-1,2,4-thiadiazol-3-yl)-2-carboxymethoxyiminoacetamido]-3-[1-methyl- 4-(3,4 -dihydroxybenzoyl)-1-piperazinio]methyl-3-cephem-4-carboxylate (syn isomer) (265 mg).

Workup

  1. customevaporated in vacuo
  2. customto remove acetone
  3. stirringstirred for 2 hours at room temperature
  4. filtrationfiltered
  5. customThe eluate was evaporated in vacuo
  6. customto remove isopropyl alcohol

Sources & evidence

ORD record
ord-f4345a74ec244280bbde5ecfe6b6d5cb
Source dataset
uspto-grants-1996_07
Patent number
US05532354

Reaction notes

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