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Sodium Hydroxide → HCID 117720296、化合物

HRID 530249
ノート
印刷プレビュー

反応式

HRID 530249 の反応式
[CH:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([C@@H:13]3[C@@H:18]([CH3:19])[CH2:17][CH2:16][CH2:15][C:14]3([CH3:21])[CH3:20])=[O:12])=[CH:8][CH:9]=2)[CH:4]=[CH:3][N:2]=1.[OH-].[Na+]>C(O)(=O)C.ClCCl.[Pt](=O)=O>[CH2:1]1[C:10]2[C:5](=[CH:6][C:7]([C:11]([C@@H:13]3[C@@H:18]([CH3:19])[CH2:17][CH2:16][CH2:15][C:14]3([CH3:20])[CH3:21])=[O:12])=[CH:8][CH:9]=2)[CH2:4][CH2:3][NH:2]1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 14798Sodium HydroxideHCID 117720150HCID 117720150、化合物

生成物 1

HCID 117720296HCID 117720296、化合物収率 72.3%

試薬・触媒・溶媒 3

HCID 345198Adams' catalyst触媒HCID 176Acetic Acid溶媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of the product of Example 13a (178 mg, 0.63 mmol) in acetic acid (2 mL) was added platinum dioxide (25 mg) and the reaction was stirred at room temperature under an atmosphere of hydrogen for 4 hours. The mixture was diluted with dichloromethane (40 mL) and basified with 1 N NaOH (35 mL) and the organic phase was separated. The aqueous layer was extracted with dichloromethane (30 mL). The combined organic phase was washed with brine (50 mL), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=50/1->10/1) to afford the title compound as a dark brown oil (130 mg, Yield: 72%). 1H NMR (400 MHz, CDCl3) δ 7.76 (d, J=8.4 Hz, 1H), 7.73 (s, 1H), 7.13 (d, J=8.4 Hz, 1H), 4.18 (s, 2H), 3.28 (t, J=6.2 Hz, 2H), 3.01 (t, J=6.2 Hz, 2H), 2.11-2.02 (m, 1H), 1.81-1.77 (m, 1H), 1.61-1.54 (m, 2H), 1.44-1.41 (m, 1H), 1.34-1.24 (m, 3H), 1.10-0.98 (m, 4H), 0.77 (s, 3H), 0.74 (d, J=6.4 Hz, 3H) ppm; Mass spectrum (ESI +ve) m/z 286 (M+H+).

後処理

  1. customthe organic phase was separated
  2. extractionThe aqueous layer was extracted with dichloromethane (30 mL)
  3. washThe combined organic phase was washed with brine (50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography (eluent: dichloromethane/methanol=50/1->10/1)

出典と根拠

ORDレコード
ord-6ada8abf14f24b41a75d600a059cca76
出典データセット
uspto-grants-2016_05
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09353063B2

反応ノート

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