Benzyl mercaptan → HCID 14501363、化合物

HRID 1904599ノート

反応式

HRID 1904599 の反応式
[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

参加物

6

反応物 3

HCID 7509Benzyl mercaptan2 回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

生成物 1

HCID 14501363HCID 14501363、化合物

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 517045Sodium Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-8460c4134be64302b1190f2ea1b9f1f6
出典データセット
uspto-grants-1989_06
特許番号
US04839355

反応ノート

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