Hydrochloric Acid → HCID 131716078, compound

HRID 1074364Notes

Reaction equation

HRID 1074364 reaction equation
FC(F)(F)C(O)=O.[CH:8]1([O:11][N:12]=[C:13]([C:39]2[N:40]=[C:41]([NH:44]C=O)[S:42][CH:43]=2)[C:14]([NH:16][C@@H:17]2[C:37](=[O:38])[N:19]3[C:20]([C:34]([O-:36])=[O:35])=[C:21]([CH2:24][N+:25]4[CH:30]=[CH:29][C:28]([C:31](=[O:33])[NH2:32])=[CH:27][CH:26]=4)[CH2:22][S:23][C@H:18]23)=[O:15])[CH2:10][CH2:9]1.Cl.C(=O)(O)[O-].[Na+]>CO.O1CCCC1>[NH2:44][C:41]1[S:42][CH:43]=[C:39]([C:13](=[N:12][O:11][CH:8]2[CH2:9][CH2:10]2)[C:14]([NH:16][C@@H:17]2[C:37](=[O:38])[N:19]3[C:20]([C:34]([O-:36])=[O:35])=[C:21]([CH2:24][N+:25]4[CH:30]=[CH:29][C:28]([C:31](=[O:33])[NH2:32])=[CH:27][CH:26]=4)[CH2:22][S:23][C@H:18]23)=[O:15])[N:40]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 6422Trifluoroacetic acidHCID 516892Sodium BicarbonateHCID 131716074HCID 131716074, compound

Product 1

HCID 131716078HCID 131716078, compoundYield 11.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of trifluoroacetic acid salt of 7β-[2-cyclopropyloxyimino-2-(2-formamidothiazol-4-yl)acetamido]-3-(4-carbamoyl-l-pyridinio)methyl-3-cephem-4-carboxylate (syn isomer) (1.6 g) and concentrated hydrochloric acid (0.76 ml) in a mixture of methanol (16 ml) and tetrahydrofuran (5 ml) was warmed at 33° to 35° C. for 1.5 hours. The mixture was poured into ice-water, adjusted to pH 2.5 with saturated aqueous solution of sodium bicarbonate and washed with ethyl acetate. The aqueous solution was subjected to column chromatography on a non-ionic adsorption resin "Diaion HP-20" (30 ml). After the column was washed with water (300 ml), 1% isopropyl alcohol (60 ml), and 3% isopropyl alcohol (60 ml) successively, the elution was carried out with 5% isopropyl alcohol (250 ml) and 10% isopropyl alcohol (150 ml) successively. The fractions containing the object compound were collected, combined, concentrated in vacuo to about 100 ml and lyophylized to give 7β-[2-(2-aminothiazol-4-yl)-2-(cyclopropyloxyimino)acetamido]-3-(4-carbamoyl-1-pyridinio)methyl-3-cephem-4-carboxylate (syn isomer) (180 mg).

Workup

  1. temperaturewas warmed at 33° to 35° C. for 1.5 hours
  2. washwashed with ethyl acetate
  3. washAfter the column was washed with water (300 ml), 1% isopropyl alcohol (60 ml), and 3% isopropyl alcohol (60 ml) successively
  4. washthe elution
  5. additionThe fractions containing the object compound
  6. customwere collected
  7. concentrationconcentrated in vacuo to about 100 ml

Sources & evidence

ORD record
ord-e60dc06cda5f40eda2ba50e847e70192
Source dataset
uspto-grants-1990_11
Patent number
US04973699

Reaction notes

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