Potassium Hydroxide → (R)-(+)-2-(4-chlorophenyl)-3,4-dihydro-2H-1,4-benzothiazine

HRID 5839

反応式

HRID 5839 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@@H:8]2[CH2:13][N:12](C(=O)[C@@H]3CCCN3S(C3C=CC4C(=CC=CC=4)C=3)(=O)=O)[C:11]3[CH:34]=[CH:35][CH:36]=[CH:37][C:10]=3[S:9]2)=[CH:4][CH:3]=1.[OH-].[K+]>C(O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@@H:8]2[CH2:13][NH:12][C:11]3[CH:34]=[CH:35][CH:36]=[CH:37][C:10]=3[S:9]2)=[CH:6][CH:7]=1

参加物

4

反応物 2

HCID 14797Potassium HydroxideHCID 54249707(R)-2-(4-Chlorophenyl)-4-[(S)-N-(2-naphthalene-sulfonyl)prolyl]-3,4-dihydro-2H-1,4-benzothiazine

生成物 1

HCID 22847494(R)-(+)-2-(4-chlorophenyl)-3,4-dihydro-2H-1,4-benzothiazine収率 58.7%

試薬・触媒・溶媒 1

HCID 19096565Water ethanol溶媒

実験手順

(R)-2-(4-Chlorophenyl)-4-[(S)-N-(2-naphthalenesulfonyl)prolyl]-3,4-dihydro-2H-1,4-benzothiazine (9.40 g, 0.017 mole) is suspended in ethanol-water (10:1, 188 ml), and thereto is added 86 % potassium hydroxide (11.2 g, 0.172 mole), and the mixture is refluxed for 30 minutes. The reaction mixture is poured into ice water and the mixture is extracted with ethyl acetate. The ethyl acetate layer is washed with water and saline, dried over sodium sulfate and distilled to remove the solvent. The residue is purified by silica gel column chromatography (CHCl3) and thereafter recrystallized from ethyl acetate-hexane twice to give (R)-(+)-2-(4-chlorophenyl)-3,4-dihydro-2H-1,4-benzothiazine (2.61 g, 58%).

後処理

  1. temperaturethe mixture is refluxed for 30 minutes
  2. extractionthe mixture is extracted with ethyl acetate
  3. washThe ethyl acetate layer is washed with water and saline
  4. dry with materialdried over sodium sulfate
  5. distillationdistilled
  6. customto remove the solvent
  7. customThe residue is purified by silica gel column chromatography (CHCl3)
  8. customrecrystallized from ethyl acetate-hexane twice

出典と根拠

ORDレコード
ord-29f1c7d529084af1a2d53d160d01362e
出典データセット
uspto-grants-1993_09
特許番号
US05246929

関連ノート

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