Acetic Acid → 16beta-Azido-3-methoxy-estra-1,3,5(10)-triene-17alpha-ol

HRID 1050283노트

반응식

HRID 1050283 반응식
[O:1]1[C@H:3]2[C@:4]3([CH2:19][CH2:18][C@H:17]4[C@@H:8]([CH2:9][CH2:10][C:11]5[CH:12]=[C:13]([O:20][CH3:21])[CH:14]=[CH:15][C:16]=54)[C@@H:6]3[CH2:7][C@@H:2]12)[CH3:5].[N-:22]=[N+:23]=[N-:24].[Na+].CS(C)=O.C(O)(=O)C>O>[N:22]([C@H:2]1[CH2:7][C@H:6]2[C@H:8]3[C@H:17]([CH2:18][CH2:19][C@:4]2([CH3:5])[C@@H:3]1[OH:1])[C:16]1[CH:15]=[CH:14][C:13]([O:20][CH3:21])=[CH:12][C:11]=1[CH2:10][CH2:9]3)=[N+:23]=[N-:24]

참가 물질

6

반응물 4

HCID 176Acetic AcidHCID 679Dimethyl SulfoxideHCID 33557Sodium AzideHCID 1257692916alpha,17alpha-Epoxy-3-methoxy-1,3,5(10)-estratriene

생성물 1

HCID 2172340316beta-Azido-3-methoxy-estra-1,3,5(10)-triene-17alpha-ol수율 73%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

5.0 g of 16α,17α-epoxy-3-methoxy-estra-1,3,5(10)-triene, 20 g sodium azide, 100 ml abs. DMSO and 30 ml glacial acetic acid are stirred at 110° C. 7 h under argon atmosphere. The mixture is then poured into water, extracted with ether, washed with 1N NaOH and then with water. After drying and removal of the solvent by distillation, the residue is chromatographed with benzene on 50 g aluminum oxide (neutral, activity level 1). Recrystallization from methanol/water yields 4.2 g (73%) of the azide.

후처리

  1. custom7 h
  2. extractionextracted with ether
  3. washwashed with 1N NaOH
  4. customAfter drying
  5. customremoval of the solvent
  6. distillationby distillation
  7. customthe residue is chromatographed with benzene on 50 g aluminum oxide (neutral, activity level 1)
  8. customRecrystallization from methanol/water

출처 및 근거

ORD 기록
ord-47bb47210a2a47acac96530a900cebb2
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382288B2

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