1-Methylimidazole → HCID 131734116, compound

HRID 1508630Notes

Reaction equation

HRID 1508630 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[C:5]([Cl:9])=[CH:4][C:3]=1[S:10](Cl)(=[O:12])=[O:11].CN1C=CN=C1.[C:20]([O:28][CH2:29][C@@H:30]([OH:46])[C@@H:31]([O:37][C:38](=[O:45])[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1)[CH2:32][CH:33]=[N:34][O:35][CH3:36])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.C(OCC)(=O)C>C(#N)C.O>[C:20]([O:28][CH2:29][C@@H:30]([O:46][S:10]([C:3]1[CH:4]=[C:5]([Cl:9])[C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1])(=[O:12])=[O:11])[C@@H:31]([O:37][C:38](=[O:45])[C:39]1[CH:40]=[CH:41][CH:42]=[CH:43][CH:44]=1)[CH2:32][CH:33]=[N:34][O:35][CH3:36])(=[O:27])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

7

Reactant 4

HCID 13901-MethylimidazoleHCID 8857Ethyl AcetateHCID 275752,4,5-Trichlorobenzenesulfonyl chlorideHCID 131734117HCID 131734117, compound

Product 1

HCID 131734116HCID 131734116, compoundYield 81.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

5.51 g of 2,4,5-trichlorobenzenesulfonyl chloride and 2.14 mL of 1-methylimidazole were added to a solution of 6.65 g of (2R,3S)-2-hydroxy-5-(methoxyimino)pentane-1,3-diyl dibenzoate in 67 mL of acetonitrile at room temperature, and the obtained mixture was then stirred at room temperature for 2 hours. Thereafter, ethyl acetate and water were added to the reaction mixture. The organic layer was fractionated, and was then dried over anhydrous sodium sulfate. The solvent was distilled away under reduced pressure. 20 mL of ethyl acetate and 30 mL of hexane were added to the obtained residue, and a solid was then removed by filtration. After that, the solvent was distilled away under reduced pressure, so as to obtain 8.97 g of (2R,3S)-5-(methoxyimino)-2-(((2,4,5-trichlorophenyl)sulfonyl)oxy)pentane-1,3-diyl dibenzoate in the form of a colorless oily product.

Workup

  1. dry with materialwas then dried over anhydrous sodium sulfate
  2. distillationThe solvent was distilled away under reduced pressure
  3. addition20 mL of ethyl acetate and 30 mL of hexane were added to the obtained residue
  4. customa solid was then removed by filtration
  5. distillationAfter that, the solvent was distilled away under reduced pressure

Sources & evidence

ORD record
ord-2852106c0a0b4d938bf25aa3595042f8
Source dataset
uspto-grants-2015_12
Patent number
US09221865B2

Reaction notes

Loading…