Hydrochloric Acid → HCID 22873905, compound

HRID 1684569Notes

Reaction equation

FC(OS([C:9]1[CH2:26][CH2:25][C@@:24]2([CH3:27])[C:11](=[CH:12][CH2:13][C@@H:14]3[C@@H:23]2[CH2:22][CH2:21][C@@:19]2([CH3:20])[C@H:15]3[CH2:16][CH2:17][C@@H:18]2[C:28](=[O:38])[CH2:29][CH2:30][C:31]2[CH:36]=[CH:35][C:34]([F:37])=[CH:33][CH:32]=2)[CH:10]=1)(=O)=O)(F)F.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:58]([O-:61])(=[O:60])C.[K+].Cl>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CN(C=O)C>[F:37][C:34]1[CH:33]=[CH:32][C:31]([CH2:30][CH2:29][C:28]([C@H:18]2[CH2:17][CH2:16][C@H:15]3[C@H:14]4[C@H:23]([CH2:22][CH2:21][C@:19]23[CH3:20])[C@:24]2([CH3:27])[C:11]([CH:10]=[C:9]([C:58]([OH:61])=[O:60])[CH2:26][CH2:25]2)=[CH:12][CH2:13]4)=[O:38])=[CH:36][CH:35]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A mixture of trifluoromethyl -17β-[3-(4-fluorophenyl )-1-oxopropyl]-androsta-3,5-diene-3-sulfonate (0.28 g, 0.5 mmol), palladium (II) acetate (5.6 mg, 0.025 mmol), triphenylphosphine (13 mg, 0.05 mmol), potassium acetate (0.19 g, 2 mmol) and DMF (6 ml) was heated at 60° C. under an atmosphere of CO for 2.5 hours. The cooled mixture was diluted with ice water, acidified with dilute HCl and extracted with CH2Cl2. The organic extract was washed with water, brine, dried (MgSO4), filtered, concentrated in vacuo, and chromatographed (silica gel, 1% AcOH/19% EtOAc/80% hexanes) to yield the title compound 0.12 g (53%). Recrystallized from methanol-acetone. mp 220°-220° C. analysis for C29H35FO3 0.25 H2O(455.1)

Workup

extractionextracted with CH2Cl2
extractionThe organic extract
washwas washed with water, brine
dry with materialdried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customchromatographed (silica gel, 1% AcOH/19% EtOAc/80% hexanes)

Sources & evidence

ORD record: ord-f2b5e0ebd3894fc282b784c1772a1a27
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05641765

Reaction notes

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