Imidazole → HCID 68825044, compound

HRID 2113293Notes

Reaction equation

HRID 2113293 reaction equation
N1C=CN=C1.[CH2:6]([Si:8](Cl)([CH2:11][CH3:12])[CH2:9][CH3:10])[CH3:7].[OH:14][C@@H:15]([C@@H:17]1[C@@H:20]([C@@H:21]([CH3:40])[C:22]([C:24]2[S:28][C:27]3=[C:29]([C:32]([C:34]4[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=4)=[O:33])[N:30]=[CH:31][N:26]3[CH:25]=2)=[O:23])[NH:19][C:18]1=[O:41])[CH3:16]>CN(C)C=O.C(OCC)(=O)C>[CH2:6]([Si:8]([CH2:11][CH3:12])([CH2:9][CH3:10])[O:14][C@@H:15]([C@@H:17]1[C@@H:20]([C@@H:21]([CH3:40])[C:22]([C:24]2[S:28][C:27]3=[C:29]([C:32]([C:34]4[CH:35]=[N:36][CH:37]=[CH:38][CH:39]=4)=[O:33])[N:30]=[CH:31][N:26]3[CH:25]=2)=[O:23])[NH:19][C:18]1=[O:41])[CH3:16])[CH3:7]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 57643916HCID 57643916, compound

Product 1

HCID 68825044HCID 68825044, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

Imidazole (0.15 g) and 0.36 ml of triethylsilylchloride were added to a solution of 0.32 g of (3S,4R)-3-[(1R)-1-hydroxyethyl]-4-[(1R)-1-methyl-2-[7-(pyridin-3-yl)carbonyl imidazo[5,1-b]thiazol-2-yl]-2-oxoethyl]azetidin-2-one in 3.2 ml of dimethylformamide under ice cooling, and the mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with 80 ml of ethyl acetate, and the diluted reaction mixture was washed three times with 20 ml of a 10% aqueous sodium chloride solution and was then washed with an a saturated aqueous sodium chloride solution and was dried over anhydrous magnesium sulfate. The solvent was removed by evaporation, the resultant solid was suspended in 4 ml of a hexane:ethyl acetate=1:1 solution and was collected by filtration to give 0.33 g of (3S,4R)-3-[(1R)-1-(triethylsilyloxy)ethyl]-4-[(1R)-1-methyl-2-[7-(pyridin-3-yl)carbonylimidazo[5,1-b]thiazol-2-yl]-2-oxoethyl]azetidin-2-one.

Workup

  1. customthe diluted reaction mixture
  2. washwas washed three times with 20 ml of a 10% aqueous sodium chloride solution
  3. washwas then washed with an a saturated aqueous sodium chloride solution
  4. dry with materialwas dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by evaporation
  6. filtrationethyl acetate=1:1 solution and was collected by filtration

Sources & evidence

ORD record
ord-5651f65259b6441da329718d0e586bd8
Source dataset
uspto-grants-2009_04
Patent number
US07524951B2

Reaction notes

Loading…