Benzyl mercaptan → HCID 14501363, compound

HRID 1904599Notes

Reaction equation

HRID 1904599 reaction equation
[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

Participants

6

Reactant 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

Product 1

HCID 14501363HCID 14501363, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 517045Sodium AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-8460c4134be64302b1190f2ea1b9f1f6
Source dataset
uspto-grants-1989_06
Patent number
US04839355

Reaction notes

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