Methanol → HCID 70565434, compound

HRID 2286323Notes

Reaction equation

HRID 2286323 reaction equation
[F:1][C@:2]12[C@@H:19]([OH:20])[CH2:18][C@@:16]3([CH3:17])[C@@H:12]([CH2:13][CH:14]=[C:15]3[S:21][CH3:22])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:24])[CH:4]=[CH:5][C:6](=[O:23])[CH:7]=1.CO.[Cl:27]Cl.C(=O)(O)[O-].[Na+]>ClCCl.C(Cl)(Cl)Cl>[Cl:27][C:14]1[CH2:13][C@H:12]2[C@H:11]3[C@:2]([F:1])([C@@H:19]([OH:20])[CH2:18][C@:16]2([CH3:17])[C:15]=1[S:21][CH3:22])[C@:3]1([CH3:24])[C:8](=[CH:7][C:6](=[O:23])[CH:5]=[CH:4]1)[CH2:9][CH2:10]3

Participants

7

Reactant 4

HCID 887MethanolHCID 24526ChlorineHCID 516892Sodium BicarbonateHCID 14823699HCID 14823699, compound

Product 1

HCID 70565434HCID 70565434, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 9-fluoro-11β-hydroxy-17-(methylthio)androsta-1,4,16-trien-3-one (100 mg) in a mixture of dry dichloromethane (10 ml) and methanol (8 ml) is added a 0.31 molar solution of chlorine in dichloromethane (1.0 ml). After a few hours, the solution is poured into a dilute sodium bicarbonate solution. The product is isolated by extraction with chloroform and the chloroform solution is washed with water, dried (anhydrous MgSO4) evaporated and the residue is purified by preparative thin layer chromatography to afford the title compound (35 mg), melting point 262°-268° C.

Workup

  1. waitAfter a few hours
  2. washthe chloroform solution is washed with water
  3. dry with materialdried (anhydrous MgSO4)
  4. customevaporated
  5. customthe residue is purified by preparative thin layer chromatography

Sources & evidence

ORD record
ord-3b55fee2c5764235b67c3b9183a9df2c
Source dataset
uspto-grants-1981_05
Patent number
US04265815

Reaction notes

Loading…