Phthalimide → HCID 58027624、化合物

HRID 875540ノート

反応式

HRID 875540 の反応式
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[OH2:12].[C:13]1([CH3:23])[CH:18]=C[C:16](S(O)(=O)=O)=[CH:15][CH:14]=1.[CH2:24]1[CH2:28][O:27][CH2:26][CH2:25]1>O>[OH:12][C@@H:14]([C:15]1[CH:28]=[CH:24][CH:25]=[C:26]([OH:27])[CH:16]=1)[C@H:13]([CH3:23])[CH2:18][N:5]1[C:1](=[O:11])[C:2]2[C:3](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4]1=[O:6]

参加物

5

反応物 3

HCID 6809PhthalimideHCID 8028TetrahydrofuranHCID 521998p-Toluenesulfonic acid monohydrate

生成物 1

HCID 58027624HCID 58027624、化合物

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

A mixture of THP-protected phenol 81 (4.10 g, 8.51 mmol) and p-toluenesulfonic acid monohydrate (0.36 g, 1.9 mmol) in THF (40 mL) and water (10 mL) was stirred at room temperature for 15 hrs. Solvent was removed in vacuum, the residue was treated with 20% hexane/EtOA. The precipitate was filtered off, washed with hexane, then with 20% EtOAc/hexane. Purification of the precipitate by flash chromatography (40 to 100% EtOAc/hexane gradient) gave the phenol 82 as a white solid. Yield (1.74 g, 83%). 1H NMR (400 MHz, DMSO-d6) δ 9.21 (s, 1H), 7.76-7.83 (m, 4H), 7.05 (t, J=7.8 Hz, 1H), 6.68-6.74 (m, 2H), 6.55 (ddd, J=1.0, 2.4, 8.0 Hz, 1H), 5.26 (d, J=4.1 Hz, 1H), 4.32 (dd, J=4.1, 6.3 Hz, 1H), 3.69 (dd, J=5.1, 13.7 Hz, 1H), 3.42 (dd, J=9.8, 13.5 Hz, 1H), 2.15-2.22 (m, 1H), 0.61 (d, J=6.8 Hz, 3H).

後処理

  1. customSolvent was removed in vacuum
  2. additionthe residue was treated with 20% hexane/EtOA
  3. filtrationThe precipitate was filtered off
  4. washwashed with hexane
  5. customPurification of the precipitate by flash chromatography (40 to 100% EtOAc/hexane gradient)

出典と根拠

ORDレコード
ord-9b15b6f61ad24e74ae9cc40ca85f9fb4
出典データセット
uspto-grants-2015_03
特許番号
US08981153B2

反応ノート

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