Water → 3alpha-Hydroxy-21-morpholinoacetylthiomethyl-5alpha-pregnane-11,20-dione

HRID 1973728Notes

Reaction equation

HRID 1973728 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:26]1[CH2:31][CH2:30][N:29]([CH2:32][C:33]([OH:35])=[S:34])[CH2:28][CH2:27]1.O>CC(C)=O>[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])[CH2:13][CH2:14][S:34][C:33](=[O:35])[CH2:32][N:29]2[CH2:30][CH2:31][O:26][CH2:27][CH2:28]2)[CH2:3]1

Participants

5

Reactant 3

HCID 962WaterHCID 86734286HCID 86734286, compoundHCID 178526202HCID 178526202, compound

Product 1

HCID 867342973alpha-Hydroxy-21-morpholinoacetylthiomethyl-5alpha-pregnane-11,20-dioneYield 66.8%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3α-Hydroxy-21-methylene-5α-pregnane-11,20-dione (500 mg) was dissolved in acetone (20 ml) and the solution treated with morpholinothioacetic acid (300mg), at reflux for 3 hours. The mixture was poured into water and the emulsion extracted with either. The extracts were washed with water, dried over anhydrous sodium sulphate and evaporated to a foam (540 mg) which was purified by preparative t.l.c. in ethyl acetate/petrol (1:1). The main band gave title compound (490mg.) as a white foam. [α]D + 48° (c = 1.03).

Workup

  1. temperatureat reflux for 3 hours
  2. extractionthe emulsion extracted with either
  3. washThe extracts were washed with water
  4. dry with materialdried over anhydrous sodium sulphate
  5. customevaporated to a foam (540 mg) which
  6. customwas purified by preparative t.l.c

Sources & evidence

ORD record
ord-64b6487017454ae7848a86f5154e4aad
Source dataset
uspto-grants-1976_12
Patent number
US03998829

Reaction notes

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