Hydrochloric Acid → 220475-76-3

HRID 1635668Notes

Reaction equation

HRID 1635668 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:29])[CH2:9][NH:10][C@H:11]([CH3:28])[CH2:12][C:13]2[CH:27]=[CH:26][C:16]3[O:17][C@@H:18]([C:21]([O:23]CC)=[O:22])[CH2:19][O:20][C:15]=3[CH:14]=2)[CH:5]=[CH:6][CH:7]=1.O.Cl>C(O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C@@H:8]([OH:29])[CH2:9][NH:10][C@H:11]([CH3:28])[CH2:12][C:13]2[CH:27]=[CH:26][C:16]3[O:17][C@@H:18]([C:21]([OH:23])=[O:22])[CH2:19][O:20][C:15]=3[CH:14]=2)[CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 11200952HCID 11200952, compound

Product 1

HCID 9865284220475-76-3Yield 67.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 6-(2-(R)-((2-(R)-(3-chlorophenyl )-2-hydroxyethyl)amino)propyl)-2,3-dihydro-1,4-benzodioxin-2-(R)-carboxylate (650 mg) in ethanol (2 ml) were added water (20 ml) and concentrated hydrochloric acid (0.32 ml). This solution was stirred under reflux-heating for 5 hours while removing ethanol with Dean-Stark apparatus. After the solution was concentrated under reduced pressure, acetonitrile/water (1/1) (11 ml) was added to the residue, which was then dissolved under heating. The solution was neutralized with a 5% aqueous solution of sodium hydrogencarbonate. Acetonitrile (20 ml) was added, and the crystals precipitated were dissolved under heating. The resulting solution was filtered under heating and then cooled, and the resulting crystals were filtered to give 6-(2-(R)-((2-(R)-(3-chlorophenyl)-2-hydroxyethyl)amino )-propyl)-2,3-dihydro-1,4-benzodioxin-2-(R)-carboxylic acid (412 mg). The HPLC-2 analysis of the optical isomer showed 96.5% purity (R/S=96.5/3.5, the purity of the material optical isomer used=90.5%).

Workup

  1. temperatureunder reflux-heating for 5 hours
  2. customwhile removing ethanol with Dean-Stark apparatus
  3. concentrationAfter the solution was concentrated under reduced pressure, acetonitrile/water (1/1) (11 ml)
  4. additionwas added to the residue, which
  5. dissolutionwas then dissolved
  6. temperatureunder heating
  7. additionAcetonitrile (20 ml) was added
  8. customthe crystals precipitated
  9. dissolutionwere dissolved
  10. temperatureunder heating
  11. filtrationThe resulting solution was filtered
  12. temperatureunder heating
  13. temperaturecooled
  14. filtrationthe resulting crystals were filtered

Sources & evidence

ORD record
ord-0afd7fa1bc57453ca1b2d5fb2b125f09
Source dataset
uspto-grants-2003_01
Patent number
US06509482B2

Reaction notes

Loading…