Hydrochloric Acid → 3alpha-Mercaptoandrostane-6,17-dione

HRID 1912736Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1912736
C([S:4][C@@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[CH:7]([C:8](=[O:25])[CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[O:24])[CH2:6]1)(=O)C.C([S-])CC.[Na+].Cl.O>CO>[SH:4][C@@H:5]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[CH:7]([C:8](=[O:25])[CH2:9][C@@H:10]3[C@@H:19]2[CH2:18][CH2:17][C@@:15]2([CH3:16])[C@H:11]3[CH2:12][CH2:13][C:14]2=[O:24])[CH2:6]1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 46817251-Propanethiol, sodium salt (1:1)HCID 866355963alpha-Acetylthioandrostane-6,17-dione

Produkt 1

HCID 866356003alpha-Mercaptoandrostane-6,17-dioneAusbeute 100 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a suspension of 3α-acetylthioandrostane-6,17-dione (1.07 g) in MeOH (30 mL), sodium propanethiolate (0.28 g) was added and the reaction stirred for 20 minutes at room temperature. The mixture was neutralized with 1N HCl. Water was added and the mixture extracted with EtOAc. The organic layer was separated, washed with brine, and dried over Na2SO4 and evaporated to dryness to give 3α-mercaptoandrostane-6,17-dione (943 mg, 100%), used without further purification. 1H-NMR (300 MHz, DMSO-d6, ppm from TMS): δ 3.54 (1H, m), 2.77 (1H, m), 2.54 (1H, d), 2.45-1.10 (19H, m), 0.78 (3H, s), 0.66 (3H, s).

Aufarbeitung

  1. additionwas added
  2. extractionthe mixture extracted with EtOAc
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried over Na2SO4
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-a728cc7bb7474304b0b5f6f9d2b16db2
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08609644B2

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