Benzoyl chloride → HCID 59289350、化合物

HRID 2191033ノート

反応式

HRID 2191033 の反応式
[NH2:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[N:8]([C@H:11]3[C@@H:15]4[O:16][C:17]([CH3:20])([CH3:19])[O:18][C@@H:14]4[C@@H:13]([CH2:21][OH:22])[O:12]3)[N:9]=[CH:10][C:3]=12.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1>>[OH:22][CH2:21][C@@H:13]1[C@H:14]2[O:18][C:17]([CH3:19])([CH3:20])[O:16][C@H:15]2[C@H:11]([N:8]2[C:4]3=[N:5][CH:6]=[N:7][C:2]([NH:1][C:23](=[O:30])[C:24]4[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=4)=[C:3]3[CH:10]=[N:9]2)[O:12]1

参加物

3

反応物 2

HCID 7412Benzoyl chlorideHCID 59289319((3aR,4R,6R,6aR)-6-(4-amino-1H-pyrazolo[3,4-d]pyrimidin-1-yl)-2,2-dimethyl-tetrahydrofuro[3,4-d][1,3]dioxol-4-yl)methanol

生成物 1

HCID 59289350HCID 59289350、化合物収率 49%

実験手順

Compound 22.2 (4.20 g, 13.66 mmol) in pyrdine (40 mL, 0.33 M) was cooled to 0° C. and treated with benzoyl chloride (12.68 mL, 109.3 mmol) The mixture was warmed to room temperature and stirred for 16 h. The solvent was removed in vacuo and the residue was treated with 2.5 N KOH (40 mL) in pyridine (40 mL) and stirred for 20 min. The mixture was cooled to 0° C. and AcOH was added (6 mL). The solvent was removed in vacuo and the residue was dissolved in EtOAc (150 mL) and washed with H2O (100 mL), saturated NaHCO3 (2×100 mL), and brine (100 mL). The organic layer was dried over Na2SO4, filtered, and concentrated under reduced pressure to afford compound 22.3 (2.74 g, 49% yield) as a white solid: 1H NMR (CDCl3, 300 MHz) 9.02 (br s, 1H), 8.80 (s, 1H), 8.55 (s, 1H), 7.97 (d, J=7.5 Hz, 2H), 7.62 (app t, J=7.5 Hz, 1H), 7.52 (t, J=7.5 Hz, 2H), 6.65 (s, 1H), 5.25 (m, 1H), 5.07 (d, J=6.0 Hz, 1H), 4.99 (br s, 1H), 4.53 (m, 1H), 3.91 (m, 1H), 3.77 (m, 1H), 1.61 (s, 3H), 1.35 (s, 3H); MS (ESI) m/z 412 [M+H]+.

後処理

  1. customThe solvent was removed in vacuo
  2. additionthe residue was treated with 2.5 N KOH (40 mL) in pyridine (40 mL)
  3. stirringstirred for 20 min
  4. temperatureThe mixture was cooled to 0° C.
  5. additionAcOH was added (6 mL)
  6. customThe solvent was removed in vacuo
  7. dissolutionthe residue was dissolved in EtOAc (150 mL)
  8. washwashed with H2O (100 mL), saturated NaHCO3 (2×100 mL), and brine (100 mL)
  9. dry with materialThe organic layer was dried over Na2SO4
  10. filtrationfiltered
  11. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-721ab5d1670644c882d8ca5c1e709e57
出典データセット
uspto-grants-2012_12
特許番号
US08324179B2

反応ノート

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