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

HRID 1050283ノート

反応式

HRID 1050283 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-47bb47210a2a47acac96530a900cebb2
出典データセット
uspto-grants-2016_07
特許番号
US09382288B2

反応ノート

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