Sodium Iodide → HCID 15379147, compound

HRID 1107696Notes

Reaction equation

HRID 1107696 reaction equation
[CH3:1][O:2]/[N:3]=[C:4](/[C:33]1[N:34]=[C:35]([NH:38][C:39]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[S:36][CH:37]=1)\[C:5]([NH:7][C@@H:8]1[C:31](=[O:32])[N:10]2[C:11]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)=[O:20])=[C:12](/[CH:15]=[CH:16]\[CH2:17]Cl)[CH2:13][S:14][C@H:9]12)=[O:6].[I-:58].[Na+]>CC(C)=O>[CH3:1][O:2]/[N:3]=[C:4](/[C:33]1[N:34]=[C:35]([NH:38][C:39]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[S:36][CH:37]=1)\[C:5]([NH:7][C@@H:8]1[C:31](=[O:32])[N:10]2[C:11]([C:19]([O:21][CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)=[O:20])=[C:12](/[CH:15]=[CH:16]/[CH2:17][I:58])[CH2:13][S:14][C@H:9]12)=[O:6]

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 11803547HCID 11803547, compound

Product 1

HCID 15379147HCID 15379147, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of p-methoxybenzyl 7β-[(Z)-2-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-[(Z)-3-chloro-1-propen-1-yl]3-cephem-4-carboxylate(1.5 g) dissolved in acetone(30 ml), sodium iodide(0.82 g) was added thereto under ice-cooling. The resulting solution was stirred for 15 minutes under ice-cooling and for additional 60 minutes at room temperature. The solvent was distilled off, and the residue was extracted with ethyl acetate. The extract was washed with a 10%-sodium thiosulfate and with a saturated brine, followed by drying with addition of anhydrous magnesium sulfate. The dried extract was concentrated under reduced pressure and the resulting precipitates were collected by filtration to obtain 1.2 g of p-methoxybenzyl 7β-[(Z)-2-methoxyimino-2-(2-tritylaminothiazol-4-yl)acetamido]-3-[(E)-3-iodo-1-propen-1-yl]3-cephem-4-carboxylate. The powder was dissolved in N,N-dimethylformamide(2 ml), and 5-dimethylaminomethyl-4-methylthiazole(0.31 g) was added thereto at -10° C. The resulting solution was stirred for 4 hours at -10° C. 10%-sodium thiosulfate(70 ml) was added to the reaction solution, and the resulting precipitates were collected by filtration to obtain the yellowish brown powder. The powder was stirred in 88% formic acid(1.8 ml) for an hour at 40° C., and acetone(400 ml) was added thereto. The resulting precipitates were collected by filtration and washed with acetone. The precipitates were chromatographed over silicagel [acetonitrile:distilled water 4:1(v/v)], Sephadex LH-20(or Amberlite XAD-2), and then lyophilized to obtain the target product (250 mg) as white solid.

Workup

  1. temperatureunder ice-cooling
  2. distillationThe solvent was distilled off
  3. extractionthe residue was extracted with ethyl acetate
  4. washThe extract was washed with a 10%-sodium thiosulfate and with a saturated brine
  5. dry with materialby drying with addition of anhydrous magnesium sulfate
  6. extractionThe dried extract
  7. concentrationwas concentrated under reduced pressure
  8. customthe resulting precipitates
  9. filtrationwere collected by filtration

Sources & evidence

ORD record
ord-673ada8f251c431e952fce4e5abfb618
Source dataset
uspto-grants-2000_05
Patent number
US06063778

Reaction notes

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