Hydrochloric Acid → 17-Cyclopropylcarbonyl-16-methyl-11-[4-(3-pyridinyl)phenyl]estra-4,9-dien-3-one hydrochloride

HRID 638813Notes

Reaction equation

HRID 638813 reaction equation
[CH:1]1([C:4]([C@H:6]2[C@H:11]([CH3:12])[CH2:10][C@H:9]3[C@H:13]4[C:22]([C@@H:23]([C:25]5[CH:30]=[CH:29][C:28]([C:31]6[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=6)=[CH:27][CH:26]=5)[CH2:24][C@:7]23[CH3:8])=[C:21]2[C:16](=[CH:17][C:18](=[O:37])[CH2:19][CH2:20]2)[CH2:15][CH2:14]4)=[O:5])[CH2:3][CH2:2]1.[ClH:38].O>C(#N)C>[ClH:38].[CH:1]1([C:4]([CH:6]2[CH:11]([CH3:12])[CH2:10][C@H:9]3[C@H:13]4[C:22]([CH:23]([C:25]5[CH:26]=[CH:27][C:28]([C:31]6[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=6)=[CH:29][CH:30]=5)[CH2:24][C@:7]23[CH3:8])=[C:21]2[C:16](=[CH:17][C:18](=[O:37])[CH2:19][CH2:20]2)[CH2:15][CH2:14]4)=[O:5])[CH2:3][CH2:2]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 962WaterHCID 11306419(11beta,16alpha,17beta)-17-Cyclopropylcarbon-yl-16-methyl-11-[4-(3-pyridinyl)phenyl]estra-4,9-dien-3-one

Product 1

HCID 6963627617-Cyclopropylcarbonyl-16-methyl-11-[4-(3-pyridinyl)phenyl]estra-4,9-dien-3-one hydrochloride

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (11β,16α,17β)-17-cyclopropylcarbonyl-16-methyl-11-[4-(3-pyridinyl)phenyl]estra-4,9-dien-3-one (40 mg, 0.081 mmol) in acetonitrile (1 mL) were added 2 N hydrochloric acid (40 μL) and water (5 mL). Lyophilisation of this mixture gave 11β,16α,17β)-17-cyclopropylcarbonyl-16-methyl-11-[4-(3-pyridinyl)phenyl]estra-4,9-dien-3-one hydrochloride in quantitative yield (40 mg, 0.08 mmol). 1H NMR (400 MHz, CDCl3): δ 0.34 (s, 3H), 0.80-2.85 (m, 24H), 4.47 (d, J=7 Hz, 1H), 5.81 (s, 1H), 7.31-7.35 (m, 2H), 7.51-7.55 (m, 2H), 7.64 (dd, J=8 and 5 Hz, 1H), 8.18 (dt, J=8 and 1 Hz, 1H), 8.62 (d, J=5 Hz, 1H), 8.90 (d, J=1 Hz, 1H).

Sources & evidence

ORD record
ord-a812e2cf2d9a4c308dbd17fb55be88eb
Source dataset
uspto-grants-2010_04
Patent number
US07691836B2

Reaction notes

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