Exemestane → 140461-66-1

HRID 444667

반응식

HRID 444667 반응식
[CH3:1][C@@:2]12[C:10](=[O:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][C:13]([C:15]3[C@@:21]([CH3:22])([C@H:5]1[CH2:4][CH2:3]2)[CH:20]=[CH:19][C:17](=[O:18])[CH:16]=3)=[CH2:14].[BH4-].[Na+]>CO.O>[CH3:1][C@@:2]12[CH:10]([OH:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][C:13]([C:15]3[C@@:21]([CH3:22])([C@H:5]1[CH2:4][CH2:3]2)[CH:20]=[CH:19][C:17](=[O:18])[CH:16]=3)=[CH2:14]

참가 물질

4

반응물 2

HCID 60198Exemestane4회HCID 4311764Sodium borohydride2회

생성물 1

HCID 25171222140461-66-1

시약·촉매·용매 1

HCID 22242641Methanol--water (1/1)용매

실험 절차

17-dihydroexemestane is prepared from exemestane as described in Mareck, U. et al., Rapid Commun Mass Spectrom, 20: 1954-62, 2006 with minor modifications. Briefly, exemestane and NaBH4 are individually dissolved in methanol/water (4:1, v/v). For reduction of the 17-keto functional group of exemestane, NaBH4 is slowly added to the suspended exemestane in a 1:2 molar ratio. The mixture is left at ambient temperature for at least 1 h and then assayed by thin layer chromatography to ensure reaction completeness prior to solvent removal by vacuum. After dissolving the dry residue in 1.5M HCl, 1M KOH (500 μL) is added. The mixture is extracted by ethyl ether, dried by vacuum, and re-dissolved in 30 ml ethyl ether:hexane (1:1) at 50° C. After 3 days, the formed crystals are washed with hexane and dried by vacuum. The synthesized 17-dihydroexemestane structure is characterized by a Bruker 500 MHz nuclear magnetic resonance (NMR) spectrometer and HPLC/MS/MS, with the MS spectrum resulting in a clear peak at m/z 299 [M]+ and a daughter product at m/z 135.

후처리

  1. waitThe mixture is left at ambient temperature for at least 1 h
  2. customreaction completeness
  3. customto solvent removal by vacuum
  4. dissolutionAfter dissolving the dry residue in 1.5M HCl
  5. addition1M KOH (500 μL) is added
  6. extractionThe mixture is extracted by ethyl ether
  7. customdried by vacuum
  8. dissolutionre-dissolved in 30 ml ethyl ether:hexane (1:1) at 50° C
  9. washthe formed crystals are washed with hexane
  10. customdried by vacuum
  11. customresulting in a clear peak at m/z 299 [M]+

출처 및 근거

ORD 기록
ord-078f2edd839a40679aec2e755b2e5306
출처 데이터셋
uspto-grants-2013_07
특허 번호
US08476023B2

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