Benzyl mercaptan → HCID 14501363, Verbindung

HRID 1904599Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1904599
[CH3:1][C:2]1[CH:7]=[C:6]([C:8]2[C:9]([F:29])=[C:10](F)[C:11]3[C:21](=[O:22])[C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:19][N:13]4[C@@H:14]([CH3:18])[CH2:15][O:16][C:17]=2[C:12]=34)[CH:5]=[C:4]([CH3:30])[N:3]=1.[CH2:31]([SH:38])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1.[H-].[Na+]>O1CCCC1.C([O-])(=O)C.[Na+]>[CH2:31]([S:38][C:10]1[C:11]2[C:21](=[O:22])[C:20]([C:23]([O:25][CH2:26][CH3:27])=[O:24])=[CH:19][N:13]3[C@@H:14]([CH3:18])[CH2:15][O:16][C:17]([C:12]=23)=[C:8]([C:6]2[CH:7]=[C:2]([CH3:1])[N:3]=[C:4]([CH3:30])[CH:5]=2)[C:9]=1[F:29])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1

Komponenten

6

Edukt 3

HCID 7509Benzyl mercaptan2×HCID 24758Sodium hydrideHCID 14501359ethyl (S)-10-(2,6-dimethyl-4-pyridinyl)-8,9-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylate

Produkt 1

HCID 14501363HCID 14501363, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 517045Sodium AcetateLösungsmittel

Versuchsvorschrift

To a suspension of 2.78 g ethyl (S)-10-(2,6-dimethyl-4-pyridinyl)-8,9-difluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylate in 67 ml tetrahydrofuran cooled in an ice-bath was added 0.79 ml benzyl mercaptan, followed by 0.34 g sodium hydride (60% in oil, washed with hexane before use) portionwise, and the mixture was stirred for one hour. An additional 0.079 ml benzyl mercaptan was added and stirring continued at room temperature for 3 hours. The reaction mixture was diluted with saturated sodium acetate solution and extracted with ethyl acetate. The extract was washed with water, dried (sodium sulfate) and concentrated. The residue was crystallized from isopropyl acetate to give 1.98 g ethyl (S)-8-(benzylthio)-10-(2,6-dimethyl-4-pyridinyl)-9-fluoro-3-methyl-7-oxo-2,3-dihydro-7H-pyrido[1,2,3-de][1,4]benzoxazine-6-carboxylate, yellow solid, m.p. 175°-178° C.

Aufarbeitung

  1. temperaturecooled in an ice-bath
  2. stirringstirring
  3. waitcontinued at room temperature for 3 hours
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried (sodium sulfate)
  7. concentrationconcentrated
  8. customThe residue was crystallized from isopropyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-8460c4134be64302b1190f2ea1b9f1f6
Quelldatensatz
uspto-grants-1989_06
Patentnummer
US04839355

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