Hydrochloric Acid → N-5984

HRID 1635668ノート

反応式

HRID 1635668 の反応式
[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

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 11200952HCID 11200952、化合物

生成物 1

HCID 9865284N-5984収率 67.9%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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%).

後処理

  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

出典と根拠

ORDレコード
ord-0afd7fa1bc57453ca1b2d5fb2b125f09
出典データセット
uspto-grants-2003_01
特許番号
US06509482B2

反応ノート

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