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

HRID 1050283Notes

Reaction equation

HRID 1050283 reaction equation
[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]

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-47bb47210a2a47acac96530a900cebb2
Source dataset
uspto-grants-2016_07
Patent number
US09382288B2

Reaction notes

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