Dimethyl Sulfide → HCID 131713925, compound

HRID 1632760Notes

Reaction equation

HRID 1632760 reaction equation
ClC1C=CC=C(C(OO)=[O:9])C=1.[CH:12]([NH:14][C:15]1[S:16][CH:17]=[C:18]([C:20](=[N:47][O:48][CH3:49])[C:21]([NH:23][CH:24]2[C:45](=[O:46])[N:26]3[CH:27]([C:31]([O:33][CH:34]([CH2:40][O:41][CH:42]([CH3:44])[CH3:43])[CH2:35][O:36][CH:37]([CH3:39])[CH3:38])=[O:32])[CH:28]=[CH:29][S:30][C@H:25]23)=[O:22])[N:19]=1)=[O:13].CSC>C(Cl)Cl>[CH:12]([NH:14][C:15]1[S:16][CH:17]=[C:18]([C:20](=[N:47][O:48][CH3:49])[C:21]([NH:23][CH:24]2[C:45](=[O:46])[N:26]3[C:27]([C:31]([O:33][CH:34]([CH2:35][O:36][CH:37]([CH3:38])[CH3:39])[CH2:40][O:41][CH:42]([CH3:43])[CH3:44])=[O:32])=[CH:28][CH2:29][S:30](=[O:9])[C@H:25]23)=[O:22])[N:19]=1)=[O:13]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 70297m-Chloroperbenzoic acidHCID 131713926HCID 131713926, compound

Product 1

HCID 131713925HCID 131713925, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of m-chloroperbenzoic acid (70% purity: 3.2 g) in methylene chloride (50 ml) was dropwise added to a stirred solution of 2-isopropoxy-1-isopropoxymethylethyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-2-cephem-4-carboxylate (syn isomer, 7.5 g) in methylene chloride (75 ml) at 2° to 5° C. over 25 minutes, and stirred at 0° to 5° C. for 20 minutes. Dimethylsulfide (1 ml) was added to the resultant mixture. The resultant mixture was washed with an aqueous solution of sodium bicarbonate, and a saturated aqueous solution of sodium chloride in turn. After drying the solution over anhydrous magnesium sulfate, the solvent was evaporated under reduced pressure. The residue was triturated with diethylether (100 ml), and then the precipitates were collected by filtration to give 2-isopropoxy-1-isopropoxymethylethyl 7-[2-(2-formamidothiazol-4-yl)-2-methoxyiminoacetamido]-3-cephem-4-carboxylate-1-oxide (syn isomer, 6.77 g).

Workup

  1. washThe resultant mixture was washed with an aqueous solution of sodium bicarbonate
  2. dry with materialAfter drying the solution over anhydrous magnesium sulfate
  3. customthe solvent was evaporated under reduced pressure
  4. customThe residue was triturated with diethylether (100 ml)
  5. filtrationthe precipitates were collected by filtration

Sources & evidence

ORD record
ord-f9d1823e8f90439d94406fe969c613d5
Source dataset
uspto-grants-1984_10
Patent number
US04477447

Reaction notes

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