反応式
[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([O:14]CC[Si](C)(C)C)[C:4]=1[CH2:21][CH:22]=[C:23]([CH3:29])[CH2:24][O:25][P:26]([OH:28])[OH:27].CCN(C(C)C)C(C)C.C/C(/[O:46][Si](C)(C)C)=N\[Si](C)(C)C.C1C=C(SSC2N=CC=CC=2)N=CC=1>O1CCOCC1.O>[CH3:1][O:2][C:3]1[C:11]([CH3:12])=[C:10]2[C:6]([C:7](=[O:13])[O:8][CH2:9]2)=[C:5]([OH:14])[C:4]=1[CH2:21][CH:22]=[C:23]([CH3:29])[CH2:24][O:25][P:26](=[O:46])([OH:28])[OH:27]参加物
反応物 4
生成物 1
試薬・触媒・溶媒 2
実験手順
A solution of phosphorous acid mono-{4-[6-methoxy-7-methyl-3-oxo-4-(2-trimethylsilanyl-ethoxy)-1,3-dihydro-isobenzofuran-5-yl]-2-methyl-but-2-enyl}ester (27 mg, 0.06 mmol) in dioxane (1 mL) was stirred with DIEA (21 μL, 0.12 mmol) and N,O-bis(trimethylsilyl)acetamide (29 μL, 0.12 mmol) at room temperature for 3 hours. To the reaction solution was added 2,2′-dipyridyldisulfide (16 mg, 0.072 mmol) and the mixture was allowed to stir for an additional 2 hours at room temperature. The reaction mixture was diluted by addition of H2O and the solution was stirred for 2 more hours when it was concentrated. The residue was dissolved in a solution of 10% TFA/CH2Cl2 and stirred at room temperature for 9 hours. The reaction mixture was dried under reduced pressure and the product was purified by reverse-phase HPLC to provide the desired product as a white solid. 1H NMR (300 MHz, CD3OD) δ 1.87 (s, 3H), 2.16 (s, 3H), 3.47 (d, 2H, J=7 Hz), 3.79 (s, 3H), 4.28 (d, 2H, J=6 Hz), 5.26 (s, 2H), 5.50-5.61 (m, 1H); 31P (121.4 MHz, CD3OD) δ 0.50; MS (m/z) 357 [M−H]−.
後処理
- stirringthe solution was stirred for 2 more hours when it
- concentrationwas concentrated
- dissolutionThe residue was dissolved in a solution of 10% TFA/CH2Cl2
- stirringstirred at room temperature for 9 hours
- customThe reaction mixture was dried under reduced pressure
- customthe product was purified by reverse-phase HPLC
出典と根拠
- ORDレコード
- ord-4f80eee3c2d74cac9e656a6690474baf
- 出典データセット
- uspto-grants-2011_09
- 特許番号
- US08022083B2
関連ノート
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