Hydrochloric Acid → HCID 131718146, compound

HRID 5529Notes

Reaction equation

HRID 5529 reaction equation
C([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:43][O:44][CH3:45])[C:10]([NH:12][C@@H:13]2[C:41](=[O:42])[N:15]3[C:16]([C:38]([O-:40])=[O:39])=[C:17]([CH2:20][N+:21]4([CH3:37])[CH2:26][CH2:25][N:24]([C:27](=[O:36])[C:28]5[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([OH:35])[CH:29]=5)[CH2:23][CH2:22]4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=O.Cl.C(=O)(O)[O-].[Na+]>CO>[NH2:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[N:43][O:44][CH3:45])[C:10]([NH:12][C@@H:13]2[C:41](=[O:42])[N:15]3[C:16]([C:38]([O-:40])=[O:39])=[C:17]([CH2:20][N+:21]4([CH3:37])[CH2:26][CH2:25][N:24]([C:27](=[O:36])[C:28]5[CH:33]=[CH:32][C:31]([OH:34])=[C:30]([OH:35])[CH:29]=5)[CH2:23][CH2:22]4)[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 516892Sodium BicarbonateHCID 131718139HCID 131718139, compound

Product 1

HCID 131718146HCID 131718146, compoundYield 37.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a suspension of 7β-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-[1-methyl-4-(3,4-dihydroxybenzoyl)-1-piperazinio]methyl-3-cephem-4-carboxylate (syn isomer) (1.52 g) in methanol (9 ml) was added concentrated hydrochloric acid (1.92 ml). After being stirred at room temperature for 4 hours, the solution was poured into ice water (40 ml) and adjusted to pH 2 with a saturated aqueous solution of sodium bicarbonate. The mixture was concentrated in vacuo to remove methanol. The concentrate was adjusted to pH 2 with a saturated aqueous solution of sodium bicarbonate and subjected to column chromatography on "Diaion HP-20" (40 ml), and the elution was carried out with 40% aqueous isopropyl alcohol. The eluate was concentrated in vacuo and lyophilized to give 7β-[2-(2-aminothiazol-4-yl)-2-methoxyiminoacetamido]-3-[1-methyl-4-(3,4-dihydroxybenzoyl)-1-piperazinio]methyl-3-cephem-4-carboxylate (syn isomer) (548 mg).

Workup

  1. concentrationThe mixture was concentrated in vacuo
  2. customto remove methanol
  3. wash" (40 ml), and the elution
  4. concentrationThe eluate was concentrated in vacuo

Sources & evidence

ORD record
ord-badf125e1b9643a4b3de78dd9442d0c1
Source dataset
uspto-grants-1993_09
Patent number
US05244890

Reaction notes

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