Water → HCID 14180543, compound

HRID 1905012Notes

Reaction equation

HRID 1905012 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]3C=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])C1C=CC=CC=1.[SH-:52].[Na+].O>CN(C)C=O.C(N(C(C)C)CC)(C)C>[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:45]=[CH:46][CH:47]=[CH:48][CH:49]=3)[C:38]3[CH:39]=[CH:40][CH:50]=[CH:12][CH:13]=3)=[O:35])=[C:16]([SH:52])[CH2:17][S:18][C@H:13]12)=[O:10])[C:44]1[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=1

Participants

6

Reactant 3

HCID 962WaterHCID 28015Sodium hydrosulfideHCID 14535654HCID 14535654, compound

Product 1

HCID 14180543HCID 14180543, compoundYield 170.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 81531DiisopropylethylamineSolvent

Procedure

To a solution of 16.4 g (21.9 mM) of benzhydryl 7β-phenoxyacetamido-3-diphenylphosphoryloxy-3-cephem-4-carboxylate in 128 ml of N,N-dimethylformamide were added at -10° C. a solution of 1.93 g (24.1 mM) of 70% sodium hydrosulfide in 86 ml of N,N-dimethylformamide and 4.25 g (32.9 mM) of diisopropylethylamine, and the mixture was stirred for 45 minutes. After the reaction, 200 ml of water was added and the mixture was extracted with 200 ml of diethyl ether. The aqueous layer was adjusted to pH 2 to 3 with 0.5% hydrochloric acid and extracted with ethyl acetate (300 ml), and the extract was washed with a saturated aqueous sodium chloride solution (200 ml×2) and dried over anhydrous magnesium sulfate. The solvent was evaporated and the residue was chromatographed over silica gel column (eluent; ethyl acetate:benzene=1:2 to 2:1) to give 10.4 g of benzhydryl 7β -phenoxyacetamido-3-mercapto-3-cephem-4-carboxylate.

Workup

  1. additionwas added
  2. extractionthe mixture was extracted with 200 ml of diethyl ether
  3. extractionextracted with ethyl acetate (300 ml)
  4. washthe extract was washed with a saturated aqueous sodium chloride solution (200 ml×2)
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customThe solvent was evaporated
  7. customthe residue was chromatographed over silica gel column (eluent; ethyl acetate:benzene=1:2 to 2:1)

Sources & evidence

ORD record
ord-443febd636354cfc90f3ac65c9aa701f
Source dataset
uspto-grants-1989_06
Patent number
US04841044

Reaction notes

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