HCID 131713150, compound → HCID 131713149, compound

HRID 234189Notes

Reaction equation

HRID 234189 reaction equation
[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[O:41])[C:10]([NH:12][CH:13]2[C:39](=[O:40])[N:15]3[C:16]([C:23]([O:25]C(C4C=CC=CC=4)C4C=CC=CC=4)=[O:24])=[C:17]([CH2:20][S:21][CH3:22])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2]>C(Cl)Cl.C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>[CH:1]([NH:3][C:4]1[S:5][CH:6]=[C:7]([C:9](=[O:41])[C:10]([NH:12][CH:13]2[C:39](=[O:40])[N:15]3[C:16]([C:23]([OH:25])=[O:24])=[C:17]([CH2:20][S:21][CH3:22])[CH2:18][S:19][C@H:14]23)=[O:11])[N:8]=1)=[O:2]

Participants

5

Reactant 1

HCID 131713150HCID 131713150, compound

Product 1

HCID 131713149HCID 131713149, compoundYield 64.9%

Reagents, catalysts & solvents 3

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolventHCID 7519AnisoleSolvent

Procedure

Benzhydryl 7-[(2-formamidothiazol-4-yl)glyoxylamido]-3-methylthiomethyl-3-cephem-4-carboxylate (7.0 g) was dissolved in a solution of methylene chloride (70 ml), anisole (7 ml) and trifluoroacetic acid (14 ml), and the mixture was stirred at ambient temperature for an hour. After the solvent was removed by distillation under reduced pressure, the residue was dissolved in water, adjusted to pH 2.0 with conc. hydrochloric acid and then extracted with ethyl acetate. The extract was washed with an aqueous sodium chloride and dried over magnesium sulfate, followed by evaporation. The residue was pulverized with diisopropyl ether to obtain 7-[(2-formamidothiazol-4-yl)glyoxylamido]-3-methylthiomethyl-3-cephem-4-carboxylic acid (3.3 g).

Workup

  1. customAfter the solvent was removed by distillation under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with an aqueous sodium chloride
  5. dry with materialdried over magnesium sulfate
  6. customfollowed by evaporation

Sources & evidence

ORD record
ord-78e843fcee0e43139447ead60ecb7bad
Source dataset
uspto-grants-1997_01
Patent number
US05594132

Reaction notes

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