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

HRID 5839

반응식

HRID 5839 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 19096565Water ethanol용매

실험 절차

(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%).

후처리

  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

출처 및 근거

ORD 기록
ord-29f1c7d529084af1a2d53d160d01362e
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05246929

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