Water → HCID 73089273, compound

HRID 1075659Notes

Reaction equation

HRID 1075659 reaction equation
BrN1C(=[O:7])CCC1=O.[CH3:9][C:10]1([CH3:33])[CH:15]=[CH:14][C:13]2[CH:16]=[C:17]([S:20]([N:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:26][CH2:25][CH2:24]3)(=[O:22])=[O:21])[CH:18]=[CH:19][C:12]=2[O:11]1.O.[OH-].[Na+]>CS(C)=O.O1CCOCC1.O>[CH3:9][C:10]1([CH3:33])[CH:15]2[O:7][CH:14]2[C:13]2[CH:16]=[C:17]([S:20]([N:23]3[C:32]4[C:27](=[CH:28][CH:29]=[CH:30][CH:31]=4)[CH2:26][CH2:25][CH2:24]3)(=[O:22])=[O:21])[CH:18]=[CH:19][C:12]=2[O:11]1

Participants

7

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 67184N-bromobutanimideHCID 57245273HCID 57245273, compound

Product 1

HCID 73089273HCID 73089273, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

N-Bromosuccinimide (3.65 g, 20.5 mmol) is added to a stirred solution of Intermediate 1a (6.80 g, 19.1 mmol) in dimethylsulphoxide (70 mL) and water (0.89 g, 0.50 mmol) at 15° C. The mixture is stirred for 2 hours and then treated with a solution of sodium hydroxide (4.0 g, 100 mmol) in dioxan-water and stirred at 20° C. for 30 minutes. The mixture is concentrated to 25% volume by evaporation under reduced pressure, treated with saturated aqueous ammonium chloride solution (300 mL) and extracted with ethyl acetate (2×200 mL). The combined extracts are dried (Na2SO4), filtered and the solvent is evaporated off under reduced pressure to yield the crude product which is purified by column chromatography (silica gel, 10% acetone in hexane) to give the title compound as a yellow oil, having the following physical characteristics:

Workup

  1. stirringstirred at 20° C. for 30 minutes
  2. concentrationThe mixture is concentrated to 25% volume by evaporation under reduced pressure
  3. additiontreated with saturated aqueous ammonium chloride solution (300 mL)
  4. extractionextracted with ethyl acetate (2×200 mL)
  5. dry with materialThe combined extracts are dried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent is evaporated off under reduced pressure
  8. customto yield the crude product which
  9. customis purified by column chromatography (silica gel, 10% acetone in hexane)

Sources & evidence

ORD record
ord-137b0c3d92f746d0a5784916ebbb2c8c
Source dataset
uspto-grants-1999_05
Patent number
US05905156

Reaction notes

Loading…