Potassium ethanethioate → HCID 87709629, compound

HRID 1912744Notes

Reaction equation

HRID 1912744 reaction equation
CS(O[C@@H:6]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[CH:8]([C:9](=[O:26])[CH2:10][C@@H:11]3[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C@H:12]3[CH2:13][CH2:14][C:15]2=[O:25])[CH2:7]1)(=O)=O.[K+].[C:28]([O-:31])(=[S:30])[CH3:29]>CN(C=O)C>[C:28]([S:30][C@H:6]1[CH2:23][CH2:22][C@@:21]2([CH3:24])[CH:8]([C:9](=[O:26])[CH2:10][C@@H:11]3[C@@H:20]2[CH2:19][CH2:18][C@@:16]2([CH3:17])[C@H:12]3[CH2:13][CH2:14][C:15]2=[O:25])[CH2:7]1)(=[O:31])[CH3:29]

Participants

4

Reactant 2

HCID 23670855Potassium ethanethioateHCID 87710023HCID 87710023, compound

Product 1

HCID 87709629HCID 87709629, compoundYield 55%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of 3α-methanesulfonyloxyandrostane-6,17-dione (2.00 g) in dry DMF (25 mL), thioacetic acid potassium salt (1.20 g) was added. The mixture was heated to 70° C. for 3 h. After cooling, 5% NaH2PO4 was added and extracted with EtOAc (3×). The organic extracts were washed with brine, dried over Na2SO4 and evaporated to dryness. The residue was purified by flash chromatography (SiO2, n-hexane/EtOAc 8/2) to give 3β-acetylthioandrostane-6,17-dione in 55% yield as a yellow solid. 1H-NMR (300 MHz, acetone-d6, ppm from TMS): δ 4.50 (1H, m), 3.10 (3H, s), 2.50-0.90 (20H, m), 0.88 (3H, s), 0.77 (3H, s).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with EtOAc (3×)
  3. washThe organic extracts were washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. customThe residue was purified by flash chromatography (SiO2, n-hexane/EtOAc 8/2)

Sources & evidence

ORD record
ord-9bdfa43da37748ca879b3c5a3920aefa
Source dataset
uspto-grants-2013_12
Patent number
US08609644B2

Reaction notes

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