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Sodium ethoxide → (R)-tert-Butyl 1-(3-(3-chloro-4-cyano-2-methylphenyl)-1H-pyrazol-1-yl)propan-2-ylcarbamate

HRID 872566
ノート
印刷プレビュー

反応式

HRID 872566 の反応式
[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([C:11]2[CH:15]=[CH:14][NH:13][N:12]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[O-]CC.[Na+].CS(O[CH2:25][C@H:26]([NH:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])[CH3:27])(=O)=O>C(#N)C>[Cl:1][C:2]1[C:9]([CH3:10])=[C:8]([C:11]2[CH:15]=[CH:14][N:13]([CH2:27][C@H:26]([NH:28][C:29](=[O:30])[O:31][C:32]([CH3:33])([CH3:35])[CH3:34])[CH3:25])[N:12]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]
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

5

反応物 3

HCID 2723922Sodium ethoxideHCID 14427185(R)-2-((tert-butoxycarbonyl)amino)propyl methanesulfonateHCID 178422100HCID 178422100、化合物

生成物 1

HCID 67171349(R)-tert-Butyl 1-(3-(3-chloro-4-cyano-2-methylphenyl)-1H-pyrazol-1-yl)propan-2-ylcarbamate収率 50.8%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒2 回

反応条件

温度
0 °C

実験手順

2-chloro-3-methyl-4-(1H-pyrazol-3-yl)benzonitrile (0.5 g, 2.297 mmol) was dissolved in dry acetonitrile (5 ml) under nitrogen and cooled to 0° C. Sodium ethoxide (0.313 g, 4.59 mmol) was added and the reaction mixture was stirred for 25 min and allowed to warm up to RT. (R)-2-(tert-butoxycarbonylamino)propyl methanesulfonate (0.582 g, 2.297 mmol) was dissolved in 5 ml of dry acetonitrile and added dropwise to the reaction mixture. The reaction mixture was refluxed for 15 h and then the solvents were evaporated. The residue was taken into EtOAc, washed several times with saturated aqueous NaHCO3 and water, dried with Na2SO4 and evaporated to dryness. CombiFlash purification afforded 0.437 g of the title compound using heptane/EtOAc-system as an eluent. 1H-NMR (400 MHz; d6-DMSO): δ 1.02 (d, 3H), 1.31 (s, 9H), 2.57 (s, 3H), 3.91 (m, 1H), 4.13 (m, 2H), 6.62 (m, 1H), 6.87 (d, 1H), 7.66 (d, 1H), 7.78 (d, 1H), 7.83 (d, 1H).

後処理

  1. temperatureto warm up to RT
  2. additionadded dropwise to the reaction mixture
  3. temperatureThe reaction mixture was refluxed for 15 h
  4. customthe solvents were evaporated
  5. washwashed several times with saturated aqueous NaHCO3 and water
  6. dry with materialdried with Na2SO4
  7. customevaporated to dryness
  8. customCombiFlash purification

出典と根拠

ORDレコード
ord-cd301dde5c9344b0830433a698f60963
出典データセット
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08975254B2

反応ノート

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