Sodium Hydroxide → N-Formyl-3-methoxyestra-1,3,5(10)-trien-17beta-amine

HRID 1885783노트

반응식

HRID 1885783 반응식
[CH3:1][C@@:2]12[C:10](=O)[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=3[C@H:5]1[CH2:4][CH2:3]2.NCCC1C=CC=[CH:27][N:26]=1.[OH-:31].[Na+]>C(O)=O>[CH:27]([NH:26][C@H:10]1[CH2:9][CH2:8][C@H:7]2[C@H:6]3[C@H:12]([CH2:4][CH2:3][C@:2]12[CH3:1])[C:13]1[CH:14]=[CH:19][C:18]([O:20][CH3:21])=[CH:17][C:16]=1[CH2:15][CH2:5]3)=[O:31]

참가 물질

5

반응물 3

HCID 14798Sodium HydroxideHCID 759192-PyridineethanamineHCID 92895(+)-Estrone 3-methyl ether

생성물 1

HCID 18657691N-Formyl-3-methoxyestra-1,3,5(10)-trien-17beta-amine

시약·촉매·용매 1

HCID 284Formic Acid용매

실험 절차

A mixture of estrone methyl ether (14.2 g) and 2-(2-aminoethyl)-pyridine (24 ml, 24.4 g) is stirred and cooled in an ice bath. To this mixture, formic acid (97-98%, 11.5 ml) is added in portions. The mixture is then heated in an oil bath (180°-190° C. bath temp.) for 24 hours. The mixture is poured onto ice, treated with NaOH, and extracted with methylene chloride (3X). The extracts are dried (Na2SO4), filtered, and concentrated to give a solid. The solid is crystallized from methylene chloride-hexane to give crystals. Recrystallization from methylene chloride-acetone gives the title compound, mp 252°-253° C. preceded by yellowing. (PLA2-, diabetes)

후처리

  1. temperaturecooled in an ice bath
  2. temperatureThe mixture is then heated in an oil bath (180°-190° C. bath temp.) for 24 hours
  3. additionThe mixture is poured onto ice
  4. extractionextracted with methylene chloride (3X)
  5. dry with materialThe extracts are dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give a solid
  9. customThe solid is crystallized from methylene chloride-hexane
  10. customto give crystals
  11. customRecrystallization from methylene chloride-acetone

출처 및 근거

ORD 기록
ord-9cf9c03ee81148e980d1ebf88f1f4240
출처 데이터셋
uspto-grants-1992_09
특허 번호
US05145874

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