Phthalimide → HCID 58027624, 화합물

HRID 74367노트

반응식

HRID 74367 반응식
[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]

참가 물질

5

반응물 3

HCID 6809PhthalimideHCID 8028TetrahydrofuranHCID 521998p-Toluenesulfonic acid monohydrate

생성물 1

HCID 58027624HCID 58027624, 화합물

시약·촉매·용매 1

HCID 962Water용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-d956120d39e7416fa4f92c238a62451a
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08829244B2

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