Hydrochloric Acid → Edonerpic

HRID 7440

反応式

HRID 7440 の反応式
Cl[CH2:2][CH2:3][CH2:4][O:5][CH2:6][CH2:7][C:8]1[CH:9]=[CH:10][C:11]2[S:15][CH:14]=[CH:13][C:12]=2[CH:16]=1.Cl.[NH:18]1[CH2:21][CH:20]([OH:22])[CH2:19]1.[OH-].[Na+].Cl>CS(C)=O.C(OCC)(=O)C.O>[S:15]1[C:11]2[CH:10]=[CH:9][C:8]([CH2:7][CH2:6][O:5][CH2:4][CH2:3][CH2:2][N:18]3[CH2:21][CH:20]([OH:22])[CH2:19]3)=[CH:16][C:12]=2[CH:13]=[CH:14]1

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 27592903-Hydroxyazetidine hydrochlorideHCID 219900695-[2-(3-Chloropropyloxy)ethyl]benzo[b]thiophene

生成物 1

HCID 9901946Edonerpic収率 64.2%

試薬・触媒・溶媒 3

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
65 °C

実験手順

In 30 mL of dimethyl sulfoxide was dissolved 6.50 g of 5-[2-(3-chloropropoxy)ethyl]-1-benzothiophene, and to the solution were added 5.60 g of 3-azetidinol hydrochloride and 15.3 mL of a 5.mol/L aqueous sodium hydroxide solution, after which the resulting mixture was stirred at 65° C. for 3.5 hours. After the reaction mixture was cooled, water and ethyl acetate were added thereto and the pH was adjusted to 1 with 6 mol/L hydrochloric acid, and the aqueous layer was separated. Ethyl acetate was added to the aqueous layer and the pH was adjusted to 10 with a 5 mol/L aqueous sodium hydroxide solution, after which the organic layer was separated. The organic layer was washed with water and then a saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, and then distilled under reduced pressure to remove the solvent. The residue was purified by a column chromatography (eluent; chloroform:methanol=30:1 to 10:1) to obtain 4.77 g of 1-{3-[2-(1-benzothiophen-5-yl)ethoxy]propyl}-3-azetidinol.

後処理

  1. temperatureAfter the reaction mixture was cooled
  2. customthe aqueous layer was separated
  3. additionEthyl acetate was added to the aqueous layer
  4. customafter which the organic layer was separated
  5. washThe organic layer was washed with water
  6. dry with materiala saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate
  7. distillationdistilled under reduced pressure
  8. customto remove the solvent
  9. customThe residue was purified by a column chromatography (eluent; chloroform:methanol=30:1 to 10:1)

出典と根拠

ORDレコード
ord-ecef0c41657b40eb8c5d05201a090f57
出典データセット
uspto-grants-2006_08
特許番号
US07087594B2

関連ノート

読み込み中…