Testosterone → HCID 14981639, compound

HRID 2294781Notes

Reaction equation

HRID 2294781 reaction equation
[CH3:1][C@@:2]12[C@@H:10]([OH:11])[CH2:9][CH2:8][C@H:7]1[C@@H:6]1[CH2:12][CH2:13][C:14]3[C@@:20]([CH3:21])([C@H:5]1[CH2:4][CH2:3]2)[CH2:19][CH2:18][C:16](=[O:17])[CH:15]=3.C(N(CC)CC)C.[Cl:29][CH2:30][C:31](Cl)=[O:32].CO.O>C(Cl)Cl>[Cl:29][CH2:30][C:31]([O:11][C@H:10]1[CH2:9][CH2:8][C@H:7]2[C@H:6]3[C@H:5]([CH2:4][CH2:3][C@:2]12[CH3:1])[C@:20]1([CH3:21])[C:14](=[CH:15][C:16](=[O:17])[CH2:18][CH2:19]1)[CH2:13][CH2:12]3)=[O:32]

Participants

6

Reactant 4

HCID 6013TestosteroneHCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 22242641Methanol--water (1/1)

Product 1

HCID 14981639HCID 14981639, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Testosterone (5 mmol) was dissolved in anhydrous methylene chloride (7.0 mL) and triethylamine (5 mmol) under argon. The solution was stirred for 30 minutes in an ice-bath. Chloroacetyl chloride (10 mmol) dissolved in anhydrous methylene chloride (3 mL) was added at 0° C. and stirring was continued for 30 minutes. The reaction was then allowed to warm to room temperature and was stirred overnight. The solution was washed with 0.05N hydrochloric aqueous solution (2×10 mL) and water (2×10 mL) and dried over sodium sulfate. It was concentrated under reduced pressure to give a brown solid. It was purified by silica gel column chromatography (Davisil grade 633, 200-425 mesh, 60 Å) using chloroform/petroleum ether (2:1) as an eluent to give a white solid. Yield, 1.23 g (67%); mp 125°-126° C. (124°-125° C., Molen et al., Steroids, 6, 195-214 (1965)); UV (MeOH/H2O, 1:1) λmax 246 nm (ε=1.521×104); 1H NMR δ0.81 (s, 3 H, CH3 -19), 1.15 (s, 3 H, CH3 -18), 0.82-2.50 (m, 19 H), 4.38 (d, 2 H, CH2Cl), 4.63 (t, 1 H, H-17), 5.63 (s, 1 H, H-4); MS (EI) Calcd. m/z for C21H29O335Cl 364.1805, found, 364.1804. Calcd. m/z for C21H29O337Cl 366.1776, found, 366.1776.

Workup

  1. additionwas added at 0° C.
  2. stirringstirring
  3. waitwas continued for 30 minutes
  4. stirringwas stirred overnight
  5. washThe solution was washed with 0.05N hydrochloric aqueous solution (2×10 mL) and water (2×10 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationIt was concentrated under reduced pressure
  8. customto give a brown solid
  9. customIt was purified by silica gel column chromatography (Davisil grade 633, 200-425 mesh, 60 Å)
  10. customto give a white solid
  11. customYield

Sources & evidence

ORD record
ord-9bdf1197e2df4498b9743e48345f48cf
Source dataset
uspto-grants-1997_11
Patent number
US05691307

Reaction notes

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