Perfluorophenyl acetate → HCID 23541117、化合物

HRID 1793260ノート

反応式

HRID 1793260 の反応式
[NH2:1][CH2:2][C@:3]1([CH2:17][OH:18])[O:7][C@@H:6]([N:8]2[CH:15]=[CH:14][C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@@H:4]1[OH:16].[C:19](OC1C(F)=C(F)C(F)=C(F)C=1F)(=[O:21])[CH3:20]>CN(C)C=O>[C:19]([NH:1][CH2:2][C@:3]1([CH2:17][OH:18])[O:7][C@@H:6]([N:8]2[CH:15]=[CH:14][C:12](=[O:13])[NH:11][C:9]2=[O:10])[CH2:5][C@@H:4]1[OH:16])(=[O:21])[CH3:20]

参加物

4

反応物 2

HCID 87968Perfluorophenyl acetateHCID 23541118HCID 23541118、化合物

生成物 1

HCID 23541117HCID 23541117、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

4′-C-Aminomethyl-2′-deoxyuridine (13) (0.034 g, 0.13 mmol) was dissolved in anhydrous N,N-dimethylformamide (0.5 mL) at ambient temperature. Excess pentafluorophenyl acetate (0.88 g, 0.39 mmol) was then added directly to the reaction mixture as a solid. The resulting solution was stirred for 18 hours at ambient temperature. The solvent was then removed under vacuum and the residue re-dissolved in water and then washed with toluene. The aqueous layer was then separated and the solvent removed under vacuum. The title compound was obtained as an amorphous solid (0.032 g, 82%). δH(300 MHz, D2O) 7.68(1H, d, H-6), 6.11(1H, dd, H-1′), 5.71(1H, d, H-5), 4.44(1H, dd, H-3′), 4.49(2H, 2d, H-5′), 3.33(2H, 2d, 4′-C—CH2), 2.33(2H, m, H-2′), 1.89(3H, s, CH3CONH); δC(75.45 MHz, D2O) 175.60, 167.08, 152.43, 142.86, 102.93, 88.93, 85.57, 71.91, 63.16, 40.37, 39.15, 22.72; ES +ve m/z 300(M+H)+, 242(M−CH3CONH)+.

後処理

  1. customThe solvent was then removed under vacuum
  2. dissolutionthe residue re-dissolved in water
  3. washwashed with toluene
  4. customThe aqueous layer was then separated
  5. customthe solvent removed under vacuum

出典と根拠

ORDレコード
ord-8ed602aad6f84b358ab5d4461855826e
出典データセット
uspto-grants-2006_07
特許番号
US07078499B2

反応ノート

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