Cesium fluoride → 4(R)-(pyrimidin-2-ylsulfanylmethyl)azetidin-2-one

HRID 321940ノート

反応式

HRID 321940 の反応式
[Si]([N:8]1[C@@H:11]([CH2:12][S:13][C:14]2[N:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[CH2:10][C:9]1=[O:20])(C(C)(C)C)(C)C.[F-].[Cs+]>CO>[N:15]1[CH:16]=[CH:17][CH:18]=[N:19][C:14]=1[S:13][CH2:12][C@@H:11]1[NH:8][C:9](=[O:20])[CH2:10]1

参加物

4

反応物 2

HCID 25953Cesium fluorideHCID 54171448HCID 54171448、化合物

生成物 1

HCID 543962814(R)-(pyrimidin-2-ylsulfanylmethyl)azetidin-2-one収率 104.1%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 1-(tert-butyldimethylsilyl)-4(R)-(pyrimidin-2-ylsulfanylmethyl)azetidin-2-one (280 mg, 0.905 mmol) in MeOH (4.5 mL) was added cesium fluoride (206 mg, 1.36 mmol). The reaction mixture was stirred 1.5 h at room temperature, then concentrated under vacuum. The residue was dissolved in CH2Cl2, washed with H2O and brine, dried (MgSO4), filtered and evaporated to give 4(R)-(pyrimidin-2-ylsulfanylmethyl)azetidin-2-one (184 mg) which was used as such. 1H NMR (400 MHz, CDCl3) δ 8.52 (d, J=5.1 Hz, 2H), 7.02 (t, J=5.1 Hz, 1H), 6.13-5.93 (m,1H), 4.04-3.99 (m,1H), 3.54 (dd, J=14.0, 5.4 Hz, 1H), 3.27 (dd, J=14.0, 7.0, 1H), 3.14 (ddd, J=15.0, 5.1, 1.9 Hz, 1H), 2.78 (ddd, J=15.0, 2.2, 1.3 Hz, 1H).

後処理

  1. concentrationconcentrated under vacuum
  2. dissolutionThe residue was dissolved in CH2Cl2
  3. washwashed with H2O and brine
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated

出典と根拠

ORDレコード
ord-24acd7dddc1448dc94f95267f0786a80
出典データセット
uspto-grants-2001_04
特許番号
US06211170B1

反応ノート

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