Water → (11beta,16alpha,17beta)-17-Cyclopropylcarbonyl-16-methyl-11-[4-(3-pyridinyl)phenyl]estra-4,9-dien-3-one 3-oxime

HRID 638822Notes

Reaction equation

HRID 638822 reaction equation
Cl.[NH2:2][OH:3].O.[CH:5]1([C:8]([C@H:10]2[C@H:15]([CH3:16])[CH2:14][C@H:13]3[C@H:17]4[C:26]([C@@H:27]([C:29]5[CH:34]=[CH:33][C:32]([C:35]6[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=6)=[CH:31][CH:30]=5)[CH2:28][C@:11]23[CH3:12])=[C:25]2[C:20](=[CH:21][C:22](=O)[CH2:23][CH2:24]2)[CH2:19][CH2:18]4)=[O:9])[CH2:7][CH2:6]1>O1CCOCC1>[CH:5]1([C:8]([C@H:10]2[C@H:15]([CH3:16])[CH2:14][C@H:13]3[C@H:17]4[C:26]([C@@H:27]([C:29]5[CH:34]=[CH:33][C:32]([C:35]6[CH:36]=[N:37][CH:38]=[CH:39][CH:40]=6)=[CH:31][CH:30]=5)[CH2:28][C@:11]23[CH3:12])=[C:25]2[C:20](=[CH:21][C:22](=[N:2][OH:3])[CH2:23][CH2:24]2)[CH2:19][CH2:18]4)=[O:9])[CH2:7][CH2:6]1

Participants

5

Reactant 3

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 11306419(11beta,16alpha,17beta)-17-Cyclopropylcarbon-yl-16-methyl-11-[4-(3-pyridinyl)phenyl]estra-4,9-dien-3-one

Product 1

HCID 86614752(11beta,16alpha,17beta)-17-Cyclopropylcarbonyl-16-methyl-11-[4-(3-pyridinyl)phenyl]estra-4,9-dien-3-one 3-oximeYield 84%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Hydroxylamine hydrochloride (20 mg, 0.30 mmol) and water (1 mL) were added to a stirred solution of 100 mg (0.20 mmol) of (11β,16α,17β)-17-cyclopropylcarbonyl-16-methyl-11-[4-(3-pyridinyl)phenyl]estra-4,9-dien-3-one in dioxane (2 mL). The reaction mixture was stirred overnight at room temperature and then extracted three times with dichloromethane. The combined organic layers were dried through a phase separate filter and evaporated to dryness. Purification of the crude product by HPLC followed by lyophilisation gave (11β,16α,17β)-17-cyclopropylcarbonyl-16-methyl-11-[4-(3-pyridinyl)phenyl]estra-4,9-dien-3-one 3-oxime as an E/Z mixture (2:1) (85 mg, 0.17 mmol, 84% yield). 1H NMR (400 MHz, CDCl3): δ 0.31 and 0.32 (2×s, in total 3H), 0.83-2.95 (m, 25H), 4.37-4.42 (m, 1H), 5.89 and 6.55 (2×s, in total 1H), 7.26-7.32 (m, 2H), 7.35 (dd, J=8 and 5 Hz, 1H), 7.47-7.51 (m, 2H), 7.86 (dt, J=8 and 1 Hz, 1H), 8.57 (dd, J=5 and 1 Hz, 1H), 8.84 (d, J=1 Hz, 1H).

Workup

  1. extractionextracted three times with dichloromethane
  2. customThe combined organic layers were dried through a phase
  3. customseparate
  4. filtrationfilter
  5. customevaporated to dryness
  6. customPurification of the crude product by HPLC

Sources & evidence

ORD record
ord-9667da5ad07a4c9a8ae1d0d7b711f1fd
Source dataset
uspto-grants-2010_04
Patent number
US07691836B2

Reaction notes

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