Hydrochloric Acid → HCID 70436365, compound

HRID 256100Notes

Reaction equation

HRID 256100 reaction equation
[O:1]([CH2:8][C:9]([NH:11][C@@H:12]1[C:50](=[O:51])[N:14]2[C:15]([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]=CC=[CH:40][CH:39]=3)=[O:35])=[C:16](OP(C3C=CC=CC=3)(C3C=CC=CC=3)=O)[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[SH-:52].[Na+].[C:54]([O:58][CH2:59][CH:60]=[CH2:61])(=[O:57])[C:55]#[CH:56].Cl.C(N([CH:69]([CH3:71])C)CC)(C)C>CN(C)C=O>[O:1]([CH2:8][C:9]([NH:11][C@@H:12]1[C:50](=[O:51])[N:14]2[C:15]([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:71][CH:69]=[CH:40][CH:39]=3)=[O:35])=[C:16]([S:52]/[CH:56]=[CH:55]\[C:54]([O:58][CH2:59][CH:60]=[CH2:61])=[O:57])[CH2:17][S:18][C@H:13]12)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 28015Sodium hydrosulfideHCID 81531DiisopropylethylamineHCID 84443Propiolic acid, allyl ester (8CI)HCID 14535654HCID 14535654, compound

Product 1

HCID 70436365HCID 70436365, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a cooled (-10° C.) solution of 1.5 g (2 mM) of benzhydryl 7β-phenoxyacetamido-3-diphenylphosphoryloxy-3-cephem-4-carboxylate in 12 ml of N,N-dimethylformamide were added a solution of 177 mg (2.2 mM) of 70% sodium hydrosulfide in 8 ml of N,N-dimethylformamide and 310 mg (2.4 mM) of diisopropylethylamine, and the reaction mixture was stirred for 30 minutes. Subsequently, 330 mg (3 mM) of allyl propiolate was added at the same temperature, and the reaction mixture was stirred for 40 minutes. After the reaction, 50 ml of 0.5% hydrochloric acid was added, the mixture was extracted with 100 ml of ethyl acetate, and the extract was washed with a saturated aqueous sodium chloride solution (100 ml×2) and dried over anhydrous magnesium sulfate. The solvent was evaporated, and the residue was purified by silica gel column chromatography (eluent; ethyl acetate : n-hexane=2 : 3 to 1 : 1) to give 820 mg of benzhydryl 7β-phenoxyacetamido-3-[(Z)-2allyloxycarbonylvinylthio]-3-cephem-4-carboxylate.

Workup

  1. stirringthe reaction mixture was stirred for 40 minutes
  2. additionwas added
  3. extractionthe mixture was extracted with 100 ml of ethyl acetate
  4. washthe extract was washed with a saturated aqueous sodium chloride solution (100 ml×2)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was purified by silica gel column chromatography (eluent; ethyl acetate : n-hexane=2 : 3 to 1 : 1)

Sources & evidence

ORD record
ord-c2dd6548fc734343bd77b36ef5df2df4
Source dataset
uspto-grants-1987_10
Patent number
US04699981

Reaction notes

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