Water → 21-Acetylthiomethyl-3alpha-hydroxy-5alpha-pregnane-11,20-dione

HRID 1973727Notes

Reaction equation

HRID 1973727 reaction equation
[OH:1][C@@H:2]1[CH2:22][CH2:21][C@@:20]2([CH3:23])[C@@H:4]([CH2:5][CH2:6][C@@H:7]3[C@@H:19]2[C:18](=[O:24])[CH2:17][C@@:16]2([CH3:25])[C@H:8]3[CH2:9][CH2:10][C@@H:11]2[C:12](=[O:15])[CH:13]=[CH2:14])[CH2:3]1.O.[C:27]([OH:30])(=[S:29])[CH3:28]>>[C:27]([S:29][CH2:14][CH2:13][C:12](=[O:15])[C@@H:11]1[C@:16]2([CH3:25])[C@H:8]([C@H:7]3[C@H:19]([C:18](=[O:24])[CH2:17]2)[C@:20]2([CH3:23])[C@H:4]([CH2:3][C@H:2]([OH:1])[CH2:22][CH2:21]2)[CH2:5][CH2:6]3)[CH2:9][CH2:10]1)(=[O:30])[CH3:28]

Participants

4

Reactant 3

HCID 962WaterHCID 86734286HCID 86734286, compoundHCID 178418634HCID 178418634, compound

Product 1

HCID 8673429621-Acetylthiomethyl-3alpha-hydroxy-5alpha-pregnane-11,20-dione

Procedure

3α-Hydroxy-21-methylene-5α-pregnane-11,20-dione (300 mg) was dissolved in thioacetic acid (2 ml) and left at room temperature for 3 hours. The mixture was poured into water and the precipitated oil extracted into ethyl acetate. The organic layer was washed with saturated sodium bicarbonate and water, dried over anhydrous sodium sulphate, evaporated to a pale yellow foam and purified by preparative t.l.c. in ethyl acetate/petrol (1:1). The main band gave title compound (150 mg) as an off-white foam. [α]D + 60.5° (c 0.98).

Workup

  1. extractionthe precipitated oil extracted into ethyl acetate
  2. washThe organic layer was washed with saturated sodium bicarbonate and water
  3. dry with materialdried over anhydrous sodium sulphate
  4. customevaporated to a pale yellow foam
  5. custompurified by preparative t.l.c

Sources & evidence

ORD record
ord-c9c1b5c7d09c47d5bc9fe6c572a7b15e
Source dataset
uspto-grants-1976_12
Patent number
US03998829

Reaction notes

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