Ethanethiol → HCID 86738652, compound

HRID 2199083Notes

Reaction equation

HRID 2199083 reaction equation
[C:1]([O:4][C@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][CH2:18][CH:19]2[S:23][CH3:24])[C@H:15]2[C@@:6]1([F:27])[C@:7]1([CH3:26])[C:12]([CH2:13][CH2:14]2)=[CH:11][C:10](=[O:25])[CH:9]=[CH:8]1)(=[O:3])[CH3:2].[CH2:28]([SH:30])[CH3:29].B(F)(F)F.CCOCC.C([O-])(O)=O.[Na+]>ClCCl>[C:1]([O:4][C@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][CH2:18][C:19]2([S:30][CH2:28][CH3:29])[S:23][CH3:24])[C@H:15]2[C@@:6]1([F:27])[C@:7]1([CH3:26])[C:12]([CH2:13][CH2:14]2)=[CH:11][C:10](=[O:25])[CH:9]=[CH:8]1)(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6343EthanethiolHCID 8000Boron trifluoride etherateHCID 516892Sodium BicarbonateHCID 70545029HCID 70545029, compound

Product 1

HCID 86738652HCID 86738652, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 11β-acetyloxy-9-fluoro-17-(methylthio)androsta-1,4-diene-3-one (632 mg) in dry dichloromethane (20 ml) containing dry ethanethiol (0.6 ml) is added boron trifluoride etherate (0.25 ml). After one hour, the mixture is added to a NaHCO3 solution and extracted with chloroform. The chloroform solution is washed with water, dried (MgSO4 anhydrous), and evaporated to afford the title compound (620 mg) contaminated with a small amount of 11β-acetyloxy-9-fluoroandrosta-1,4-diene-3,17-dione. This material is used in the next step without further purification. A specimen crystallized from acetone-hexane shows melting point 140°-142° C. and a consistent nmr spectrum.

Workup

  1. extractionextracted with chloroform
  2. washThe chloroform solution is washed with water
  3. dry with materialdried (MgSO4 anhydrous)
  4. customevaporated

Sources & evidence

ORD record
ord-a1d612606f6848bfa415464159821ef3
Source dataset
uspto-grants-1982_11
Patent number
US04361559

Reaction notes

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