Sulfuric Acid → Apogossypol

HRID 1666029노트

반응식

HRID 1666029 반응식
[CH3:1][C:2]1[C:24]([C:25]2[C:26]([CH3:52])=[CH:27][C:28]3[C:38]([CH:39]([CH3:41])[CH3:40])=[C:37]([O:42]C(C)=O)[C:36]([O:46]C(C)=O)=[C:35](C=O)[C:29]=3[C:30]=2[O:31]C(C)=O)=[C:23]([O:53]C(C)=O)[C:5]2=[C:6](C=O)[C:7]([O:17]C(C)=O)=[C:8]([O:13]C(C)=O)[C:9]([CH:10]([CH3:12])[CH3:11])=[C:4]2[CH:3]=1.OS(O)(=O)=O>[OH-].[Na+]>[CH3:52][C:26]1[C:25]([C:24]2[C:2]([CH3:1])=[CH:3][C:4]3[C:9]([CH:10]([CH3:11])[CH3:12])=[C:8]([OH:13])[C:7]([OH:17])=[CH:6][C:5]=3[C:23]=2[OH:53])=[C:30]([OH:31])[C:29]2=[CH:35][C:36]([OH:46])=[C:37]([OH:42])[C:38]([CH:39]([CH3:40])[CH3:41])=[C:28]2[CH:27]=1

참가 물질

4

반응물 2

HCID 1118Sulfuric AcidHCID 35450Gossypol hexaacetate

생성물 1

HCID 454878Apogossypol수율 95%

시약·촉매·용매 1

HCID 14798Sodium Hydroxide용매

실험 절차

More specifically, the gossypol acetic acid 1 (5 g, 8.65 mmol) in 50 ml of 40% NaOH was heated under nitrogen at 90° C. for 3.5 hours in the dark. The reaction mixture was cooled and poured slowly onto ice (300 ml) and concentrated H2SO4 (35 ml) mixture to form white precipitation. The precipitation was filtered, washed with water and dried to afford apogossypol (3.8 g, 95%) as a white solid. 1H NMR (CDCl3 δ 7.61 (s, 2H), 7.50 (s, 2H), 5.93 (s, 2H), 5.27 (s, 2H), 5.13 (s, 2H), 3.88 (m, 2H), 2.12 (s, 6H), 1.55 (d, J=5.5 Hz, 12H).

후처리

  1. temperatureThe reaction mixture was cooled
  2. customto form white
  3. customprecipitation
  4. customThe precipitation
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried

출처 및 근거

ORD 기록
ord-be0e14856da841418d83d3860b5071ef
출처 데이터셋
uspto-grants-2011_10
특허 번호
US08039668B2

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