Triethylamine → Benzhydryl 7-formamido-3-hydroxy-3-cephem-4-carboxylate

HRID 704260Notes

Reaction equation

HRID 704260 reaction equation
FC(F)(F)C(OC(=O)C(F)(F)F)=O.[CH:14]([NH:16][CH:17]1[C:41](=[O:42])[N:19]2[CH:20]([C:25]([O:27][CH:28]([C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)[C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:26])[CH:21]([OH:24])[CH2:22][S:23][C@H:18]12)=[O:15].C(N(CC)CC)C>C(Cl)Cl.CS(C)=O>[CH:14]([NH:16][CH:17]1[C:41](=[O:42])[N:19]2[C:20]([C:25]([O:27][CH:28]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)=[O:26])=[C:21]([OH:24])[CH2:22][S:23][C@H:18]12)=[O:15]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 9845Trifluoroacetic anhydrideHCID 86743417Benzhydryl 7-formamido-3-hydroxycepham-4-carboxylate

Product 1

HCID 88528581Benzhydryl 7-formamido-3-hydroxy-3-cephem-4-carboxylateYield 83.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolvent2×HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
-50 °C

Procedure

A solution of trifluoroacetic anhydride (2.12 ml) in methylene chloride (5 ml) was added dropwise to a solution of dimethyl sulfoxide (1.56 g) in methylene chloride (10 ml) at -50° C. The mixture was stirred at -50° C. for 10 minutes. To the mixture was added a solution of benzhydryl 7-formamido-3-hydroxycepham-4-carboxylate (4.12 g) in methylene chloride (10 ml) and dimethyl sulfoxide (1 ml). The mixture was stirred at -50° C. for 30 minutes and triethylamine (4 ml) was added dropwise thereto at -50° C. The reaction mixture was allowed to warm up to ambient temperature, poured into ice-water and extracted with methylene chloride. The extract was washed three times with water, dried over magnesium sulfate and filtered, and the filtrate was evaporated in vacuo The residue was triturated with diisopropyl ether to give benzhydryl 7-formamido-3-hydroxy-3-cephem-4-carboxylate (3.42 g) as powder.

Workup

  1. stirringThe mixture was stirred at -50° C. for 30 minutes
  2. customat -50° C
  3. temperatureto warm up to ambient temperature
  4. extractionextracted with methylene chloride
  5. washThe extract was washed three times with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. customthe filtrate was evaporated in vacuo The residue
  9. customwas triturated with diisopropyl ether

Sources & evidence

ORD record
ord-8219465ceaa447e9920fcd19eb2e1f2b
Source dataset
uspto-grants-1991_01
Patent number
US04985555

Reaction notes

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