2-Pyridinemethanethiol → 11beta-[4-[5-[(2-Pyridinylmethyl)thio]pentyloxy]phenyl]estra-1,3,5(10)-triene-3,17beta-diol

HRID 1358870Notes

Reaction equation

HRID 1358870 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][SH:8].C[O-].[Na+].Cl[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:24]=[CH:23][C:22]([C@H:25]2[CH2:42][C@@:40]3([CH3:41])[C@@H:36]([CH2:37][CH2:38][C@@H:39]3[OH:43])[C@H:35]3[C@H:26]2[C:27]2[CH:28]=[CH:29][C:30]([OH:44])=[CH:31][C:32]=2[CH2:33][CH2:34]3)=[CH:21][CH:20]=1>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][S:8][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][O:18][C:19]1[CH:20]=[CH:21][C:22]([C@H:25]2[CH2:42][C@@:40]3([CH3:41])[C@@H:36]([CH2:37][CH2:38][C@@H:39]3[OH:43])[C@H:35]3[C@H:26]2[C:27]2[CH:28]=[CH:29][C:30]([OH:44])=[CH:31][C:32]=2[CH2:33][CH2:34]3)=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 2560712-PyridinemethanethiolHCID 10942334Sodium MethoxideHCID 7001929211beta-[4-[(5-Chloro-pentyl)oxy]phenyl]estra-1,3,5(10)-triene-3,17beta-diol

Product 1

HCID 7001918911beta-[4-[5-[(2-Pyridinylmethyl)thio]pentyloxy]phenyl]estra-1,3,5(10)-triene-3,17beta-diol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution containing 0.17 cm3 of 2-pyridine methanethiol, 81 mg of sodium methylate, 234 mg of the product obtained in Stage D of Example 3 and 4 cm3 of methanol is heated for 3 hours under reflux. The methanol is distilled off, the residue is taken up with ethyl acetate, washed with water, dried and brought to dryness under reduced pressure. 360 mg of residue is collected which is chromatographed on silica (eluant ethyl acetate-essence G 8/2) and in this way 280 mg of expected product is obtained.

Workup

  1. temperatureis heated for 3 hours
  2. temperatureunder reflux
  3. distillationThe methanol is distilled off
  4. washwashed with water
  5. customdried
  6. custom360 mg of residue is collected which
  7. customis chromatographed on silica (eluant ethyl acetate-essence G 8/2) and in this way 280 mg of expected product
  8. customis obtained

Sources & evidence

ORD record
ord-8a1d450fb51d4ea09f334cea7630d4cf
Source dataset
uspto-grants-2003_07
Patent number
US06596885B2

Reaction notes

Loading…