Methanol → 5-(3-Chlorophenyl)-3-(2-(3,4-dihydroxyphenyl)-1-methylethyl)-2-oxazolidinone

HRID 37453Notes

Reaction equation

HRID 37453 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:12][C:11](=[O:13])[N:10]([CH:14]([CH3:26])[CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22]C)=[C:18]([O:24]C)[CH:17]=3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1.B(Br)(Br)Br.CO.O>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[O:12][C:11](=[O:13])[N:10]([CH:14]([CH3:26])[CH2:15][C:16]3[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([OH:24])[CH:17]=3)[CH2:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 887Methanol2×HCID 962WaterHCID 25134Boron tribromideHCID 211923405-(3-Chlorophenyl)-3-[2-(3,4-dimethyloxyphenyl)-1-methylethyl]-2-oxazolidinone

Product 1

HCID 156692045-(3-Chlorophenyl)-3-(2-(3,4-dihydroxyphenyl)-1-methylethyl)-2-oxazolidinoneYield 92.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

Twenty grams of [R-(R*,R*)]-5-(3-chlorophenyl)-3-[2-(3,4-dimethyloxyphenyl)-1-methylethyl]-2-oxazolidinone, prepared by the procedure described in U.S. Pat. No. 5.061,727, is dissolved in 100 ml of methylene chloride and cooled to 5° C. under a stream of argon. Ten ml of boron tribromide in 10 ml of methylene chloride is added dropwise over 25 minutes. The reaction mixture is stirred for 20 minutes at 0°-5° C. One hundred and fifty ml of methyl alcohol is added over 40 minutes and the reaction is allowed to warm to room temperature over 1 hour. The solvent is removed by distillation (pot temperature 90° C.) leaving an oil in the bottom of the flask. The reaction flask is charged with 36.9 g of methyl alcohol, cooled to room temperature and 148 g of water is added over 1.5 hours. The reaction is stirred at room temperature for 72 hours, followed by cooling to 5° C. and stirring at this temperature for 1 hour. The resulting precipitate is collected, rinsed with water, and dried to give 17.1 g of the desired product (Yield 92.7% theory).

Workup

  1. temperatureto warm to room temperature over 1 hour
  2. customThe solvent is removed by distillation (pot temperature 90° C.)
  3. customleaving an oil in the bottom of the flask
  4. temperaturecooled to room temperature
  5. stirringThe reaction is stirred at room temperature for 72 hours
  6. temperatureby cooling to 5° C.
  7. stirringstirring at this temperature for 1 hour
  8. customThe resulting precipitate is collected
  9. washrinsed with water
  10. customdried

Sources & evidence

ORD record
ord-bb760042f98844848cfb287d11c1b864
Source dataset
uspto-grants-1995_05
Patent number
US05420291

Reaction notes

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