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Water → Benzyl 1-benzyl-2-oxo-6-phenyl-1,2,3,4-tetrahydro-1,7-naphthyridin-3-ylcarbamate

HRID 2221098
ノート
印刷プレビュー

反応式

HRID 2221098 の反応式
[O:1]=[C:2]1[CH:11]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:10][C:9]2[C:4](=[CH:5][N:6]=[C:7]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)[CH:8]=2)[NH:3]1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:35](Br)[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1.O>CN(C=O)C>[CH2:35]([N:3]1[C:4]2[C:9](=[CH:8][C:7]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:6][CH:5]=2)[CH2:10][CH:11]([NH:12][C:13](=[O:22])[O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:2]1=[O:1])[C:36]1[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

HCID 962WaterHCID 7498Benzyl BromideHCID 10796Cesium carbonateHCID 58671541HCID 58671541、化合物

生成物 1

HCID 11605071Benzyl 1-benzyl-2-oxo-6-phenyl-1,2,3,4-tetrahydro-1,7-naphthyridin-3-ylcarbamate収率 50.4%

試薬・触媒・溶媒 1

HCID 6228
Dimethylformamide
溶媒

反応条件

温度
50 °C

実験手順

To a solution of 3F (400 mg, 1.07 mmol) in DMF (8 mL) was added cesium carbonate (873 mg, 2.68 mmol), followed by benzyl bromide (0.38 mL, 3.21 mmol). The reaction mixture was stirred at 50° C. for 1 h. After cooling to RT, water (100 mL) was added. The reaction mixture was extracted with EtOAc (3×30 mL). During the extraction, some precipitates formed. The solid was collected by filtration and washed with EtOAc to give the title compound (250 mg). The combined organics were washed with saturated NaCl, dried over Na2SO4, filtered and concentrated. The resultant residue was purified by silica gel (40 g) column chromatography eluting with a gradient of EtOAc (0-60%) in hexane to give additional 160 mg of the title compound (total 410 mg, 83%) as a white solid. LC/MS (method A): retention time=3.55 min, (M+H)+=464.

後処理

  1. temperatureAfter cooling to RT
  2. extractionThe reaction mixture was extracted with EtOAc (3×30 mL)
  3. extractionDuring the extraction
  4. customsome precipitates formed
  5. filtrationThe solid was collected by filtration
  6. washwashed with EtOAc

出典と根拠

ORDレコード
ord-da5066a45f6e4ed9b5bd758502073685
出典データセット
uspto-grants-2008_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07368458B2

反応ノート

読み込み中…

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