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Sodium hydride → ethyl 5-((tert-butyldiphenylsilyloxy)methyl)-6-((2R,6S)-2,6-dimethylmorpholino)-7-fluorobenzo[d]isoxazole-3-carboxylate

HRID 245451
ノート
印刷プレビュー

反応式

HRID 245451 の反応式
[H-].[Na+].[Si:3]([O:20][CH2:21][C:22]1[C:23]([N:38]2[CH2:43][C@H:42]([CH3:44])[O:41][C@H:40]([CH3:45])[CH2:39]2)=[C:24]([F:37])[C:25](F)=[C:26]([C:28](=[N:34][OH:35])[C:29]([O:31][CH2:32][CH3:33])=[O:30])[CH:27]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>CN(C=O)C>[Si:3]([O:20][CH2:21][C:22]1[C:23]([N:38]2[CH2:43][C@H:42]([CH3:44])[O:41][C@H:40]([CH3:45])[CH2:39]2)=[C:24]([F:37])[C:25]2[O:35][N:34]=[C:28]([C:29]([O:31][CH2:32][CH3:33])=[O:30])[C:26]=2[CH:27]=1)([C:16]([CH3:17])([CH3:18])[CH3:19])([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 24758Sodium hydrideHCID 86658093Ethyl 2-(5-((tert-butyldiphenylsilyloxy)methyl)-4-((2R,6S)-2,6-dimethylmorpholino)-2,3-difluorophenyl)-2-(hydroxyimino)acetate2 回

生成物 1

HCID 67357675ethyl 5-((tert-butyldiphenylsilyloxy)methyl)-6-((2R,6S)-2,6-dimethylmorpholino)-7-fluorobenzo[d]isoxazole-3-carboxylate収率 66.6%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒
2 回

実験手順

Sodium hydride (0.159 g, 3.97 mmol) was suspended in 20 ml of DMF and cooled in an ice bath. Ethyl 2-(5-((tert-butyldiphenylsilyloxy)methyl)-4-((2R,6S)-2,6-dimethylmorpholino)-2,3-difluorophenyl)-2-(hydroxyimino)acetate (Intermediate 165, 1.94 g, 3.18 mmol) was dissolved in 20 ml of DMF and added to the reaction flask. The ice bath was removed and the reaction stirred at room temperature for 2 hours. The reaction was quenched with sat NH4Cl (5 ml), diluted with water and extracted three times with ethyl acetate. The organic layers were combined, washed with water and brine 5×, dried over MgSO4 and concentrated. The residue was purified by silica gel column chromatography using a gradient of hexanes to ethyl acetate to give the title compound (1.250 g, 66.6%).

後処理

  1. temperaturecooled in an ice bath
  2. additionadded to the reaction flask
  3. customThe ice bath was removed
  4. customThe reaction was quenched with sat NH4Cl (5 ml)
  5. additiondiluted with water
  6. extractionextracted three times with ethyl acetate
  7. washwashed with water and brine 5×
  8. dry with materialdried over MgSO4
  9. concentrationconcentrated
  10. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-4791e6b8174f4b8cb05ea97524bcb13c
出典データセット
uspto-grants-2014_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08658641B2

反応ノート

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