Sodium Acetate → HCID 131713174, compound

HRID 1154214Notes

Reaction equation

HRID 1154214 reaction equation
[C:1]([O:5][C:6]([N:8]([CH:25]1[C:50](=[O:51])[N:27]2[C:28]([C:34]([O:36][CH:37]([C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)[C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)=[O:35])=[C:29]([CH:32]=[CH2:33])[CH2:30][S:31][C@H:26]12)[C:9](=[O:24])[CH:10]([C:12]1[N:13]=[C:14]([NH:17]C(=O)C(F)(F)F)[S:15][CH:16]=1)[NH2:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].C([O-])(=O)C.[Na+]>O1CCCC1.CC(C)=O.O>[C:1]([O:5][C:6]([N:8]([CH:25]1[C:50](=[O:51])[N:27]2[C:28]([C:34]([O:36][CH:37]([C:38]3[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=3)[C:44]3[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=3)=[O:35])=[C:29]([CH:32]=[CH2:33])[CH2:30][S:31][C@H:26]12)[C:9](=[O:24])[CH:10]([C:12]1[N:13]=[C:14]([NH2:17])[S:15][CH:16]=1)[NH2:11])=[O:7])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 2

HCID 517045Sodium AcetateHCID 131713175HCID 131713175, compound

Product 1

HCID 131713174HCID 131713174, compoundYield 45.9%

Reagents, catalysts & solvents 3

HCID 180AcetoneSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of benzhydryl 7-[N-tert-butoxycarbonyl-2-{2-(2,2,2-trifluoroacetamido)thiazol-4-yl}glycinamido]-3-vinyl-3-cephem-4-carboxylate (2.5 g) and sodium acetate (2.8 g) in tetrahydrofuran (20 ml), acetone (20 ml) and water (40 ml) was stirred at ambient temperature for 2 hours. After the reaction mixture was evaporated, the residue was extracted with ethyl acetate. The extract was washed with an aqueous solution of sodium chloride, dried over anhydrous magnesium sulfate and then evaporated to give a residue, which was subjected to column chromatography on silica gel (50 g). Elution was carried out with methylene chloride and then a mixture of methylene chloride and diethyl ether (9:1 by volume), and the fractions containing the desired compound were collected and evaporated to give benzhydryl 7-[N-tert-butoxycarbonyl-2-(2-aminothiazol-4-yl)glycinamido]-3-vinyl-3-cephem-4-carboxylate (1.0 g).

Workup

  1. customAfter the reaction mixture was evaporated
  2. extractionthe residue was extracted with ethyl acetate
  3. washThe extract was washed with an aqueous solution of sodium chloride
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customevaporated
  6. customto give a residue, which
  7. washElution
  8. additiona mixture of methylene chloride and diethyl ether (9:1 by volume)
  9. additionthe fractions containing the desired compound
  10. customwere collected
  11. customevaporated

Sources & evidence

ORD record
ord-5c9544bca1b44af9915a813835bb92ef
Source dataset
uspto-grants-1984_12
Patent number
US04487927

Reaction notes

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