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

HRID 1358870Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1358870
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-8a1d450fb51d4ea09f334cea7630d4cf
Quelldatensatz
uspto-grants-2003_07
Patentnummer
US06596885B2

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