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Ammonia → HCID 67364108, compound

HRID 1472954
Notes
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Reaction equation

HRID 1472954 reaction equation
[CH:1]([O:8][CH2:9][CH3:10])(OCC)OCC.C(O[C@@H:15]1[C@H:21]2[C@H:22]3[C@H:31]([CH2:32][CH2:33][C@:18]2([CH2:19][CH3:20])[C:17](=[O:35])[CH2:16]1)[C@@H:30]1[C:25](=[CH:26]C(=O)[CH2:28][CH2:29]1)[CH2:24][CH2:23]3)(=O)C.N.C(OCC)(=O)C>CCO.C1(C)C=CC(S(O)(=O)=O)=CC=1.O>[CH2:9]([O:8][C:1]1[CH2:28][CH2:29][C@H:30]2[C:25](=[CH:24][CH2:23][C@@H:22]3[C@@H:31]2[CH2:32][CH2:33][C@@:18]2([CH2:19][CH3:20])[C@H:21]3[CH:15]=[CH:16][C:17]2=[O:35])[CH:26]=1)[CH3:10]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 222AmmoniaHCID 8857Ethyl AcetateHCID 31214Ethyl orthoformateHCID 67361589Gestodene Impurity 1

Product 1

HCID 67364108HCID 67364108, compoundYield 56%

Reagents, catalysts & solvents 3

HCID 6101
p-Toluenesulfonic acid
Catalyst
HCID 702EthanolSolvent
HCID 962WaterSolvent

Procedure

Triethyl orthoformate (3 ml, 18 mmol) and p-Toluenesulfonic acid (30 mg, 0.16 mmol) were added to a suspension of 15α-acetoxy-18-methyl-estr-4-en-3,17-dione (3 g, 8.8 mmol) in EtOH (18 ml). The mixture was stirred at room temperature for 1 h. Ammonia 32% (15.4 ml, 145 mmol) was added, and the mixture was heated at 40° C. for 48 h, cooled to 10° C., and ethyl acetate and water (15 ml) were then added. The extract was washed with water and concentrated. The crude product was purified by flash chromatography, eluting with heptane and ethyl acetate (8:2), crystallized from heptane, and dried under vacuum to afford 3-ethoxy-18-methyl-estra-3,5,15-trien-17-one (1.54 g, yield: 56%).

Workup

  1. temperaturethe mixture was heated at 40° C. for 48 h
  2. temperaturecooled to 10° C.
  3. washThe extract was washed with water
  4. concentrationconcentrated
  5. customThe crude product was purified by flash chromatography
  6. washeluting with heptane and ethyl acetate (8:2)
  7. customcrystallized from heptane
  8. customdried under vacuum

Sources & evidence

ORD record
ord-edd664a4d3b5404cb0c94275c0b0239d
Source dataset
uspto-grants-2015_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09012667B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes