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

HRID 5839

Reaktionsgleichung

Reaktionsgleichung von HRID 5839
[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

Komponenten

4

Edukt 2

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

Produkt 1

HCID 22847494(R)-(+)-2-(4-chlorophenyl)-3,4-dihydro-2H-1,4-benzothiazineAusbeute 58,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 19096565Water ethanolLösungsmittel

Versuchsvorschrift

(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%).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-29f1c7d529084af1a2d53d160d01362e
Quelldatensatz
uspto-grants-1993_09
Patentnummer
US05246929

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