Sulfuric Acid → HCID 9955725, compound

HRID 2304886Notes

Reaction equation

HRID 2304886 reaction equation
[C:1](Cl)(=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[OH:14][C@H:15]1[CH2:20][CH2:19][C@H:18]2[C@H:21]3[C@H:30]([CH2:31][CH2:32][C@:16]12[CH3:17])[C@@H:29]1[C:24](=[CH:25][C:26](=[O:33])[CH2:27][CH2:28]1)[CH2:23][C@H:22]3[CH3:34].OS(O)(=O)=O>>[CH3:34][C@@H:22]1[CH2:23][C:24]2[C@H:29]([CH2:28][CH2:27][C:26](=[O:33])[CH:25]=2)[C@@H:30]2[C@@H:21]1[C@H:18]1[C@@:16]([CH2:32][CH2:31]2)([CH3:17])[C@@H:15]([O:14][C:1](=[O:12])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11])[CH2:20][CH2:19]1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 87287Undecanoyl chlorideHCID 9838899Trestolone

Product 1

HCID 9955725HCID 9955725, compound

Procedure

A total of 2.23 grams of commercially available undecanoyl chloride were added to a stirred solution of 1.58 grams of (7α,17β)-17-hydroxy-7-methylestr-4-en-3-one at 0-5° C. reaction mixture was allowed to reach room temperature and stirred overnight. Thereafter, ice was added and after stirring for another 2 hours the reaction mixture was poured into ice-water, containing 4 ml of conc. H2SO4, followed by ethyl acetate extraction. The organic layers were washed with water, cold 1 N NaOH solution and brine, dried on sodium sulfate, filtered and evaporated in vacuo. The residue was chromatographed over silica. Elution with heptane-ethylacetate (4:1) and evaporation gave a greasy solid that was collected. Yield 1.42 g, [α]D20=+36° (c=1; dioxane), MS (ESI): 456.

Workup

  1. customreaction mixture
  2. customto reach room temperature
  3. additionThereafter, ice was added
  4. stirringafter stirring for another 2 hours the reaction mixture
  5. extractionfollowed by ethyl acetate extraction
  6. washThe organic layers were washed with water, cold 1 N NaOH solution and brine
  7. customdried on sodium sulfate
  8. filtrationfiltered
  9. customevaporated in vacuo
  10. customThe residue was chromatographed over silica
  11. washElution
  12. customwith heptane-ethylacetate (4:1) and evaporation
  13. customgave a greasy solid
  14. customthat was collected

Sources & evidence

ORD record
ord-2c15027d5fec4dc3b0b5592732699a86
Source dataset
uspto-grants-2002_08
Patent number
US06437158B1

Reaction notes

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