Sodium Iodide → HCID 88259981, compound

HRID 1107699Notes

Reaction equation

HRID 1107699 reaction equation
[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:36]/[O:37][CH3:38])/[C:8]([NH:10][C@@H:11]2[C:34](=[O:35])[N:13]3[C:14]([C:22]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)=[O:23])=[C:15](/[CH:18]=[CH:19]\[CH2:20]Cl)[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1.[I-:39].[Na+]>CC(C)=O>[NH2:1][C:2]1[S:6][N:5]=[C:4](/[C:7](=[N:36]/[O:37][CH3:38])/[C:8]([NH:10][C@@H:11]2[C:34](=[O:35])[N:13]3[C:14]([C:22]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][CH:27]=4)=[O:23])=[C:15](/[CH:18]=[CH:19]/[CH2:20][I:39])[CH2:16][S:17][C@H:12]23)=[O:9])[N:3]=1

Participants

4

Reactant 2

HCID 5238Sodium IodideHCID 139844129HCID 139844129, compound

Product 1

HCID 88259981HCID 88259981, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of p-methoxybenzyl 7β[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-[(Z)-3-chloro-1-propen-1-yl]3-cephem-4-carboxylate(1.5 g) dissolved in acetone(20 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 an hour 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 1.1 g of p-methoxybenzyl 7β-[(Z)-2-(5-amino-1,2,4-thiadiazol-3-yl)-2-methoxyiminoacetamido]-3-[(E)-3-iodo-1-propen-1-yl]3-cephem-4-carboxylate. The powder was dissolved in N,N-dimethylformamide(2.5 ml), and 4-ethylmethylamino-2-butenylamide(0.2 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(1.3 ml) for 3 hours at room temperature, 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 (180 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-4ad4b2e2d2c844f59af2216dc94f3386
Source dataset
uspto-grants-2000_05
Patent number
US06063778

Reaction notes

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