21-Bromo-5alpha-pregnane-3,11,20-trione → 21-Morpholinoacetylthio-5alpha-pregnane-3,11,20-trione

HRID 1077024Notes

Reaction equation

HRID 1077024 reaction equation
Br[CH2:2][C:3](=[O:25])[C@@H:4]1[C@:21]2([CH3:22])[C@H:7]([C@H:8]3[C@H:18]([C:19](=[O:23])[CH2:20]2)[C@:16]2([CH3:17])[C@H:11]([CH2:12][C:13](=[O:24])[CH2:14][CH2:15]2)[CH2:10][CH2:9]3)[CH2:6][CH2:5]1.[O:26]1[CH2:31][CH2:30][N:29]([CH2:32][C:33]([OH:35])=[S:34])[CH2:28][CH2:27]1>CC(C)=O>[O:26]1[CH2:31][CH2:30][N:29]([CH2:32][C:33]([S:34][CH2:2][C:3](=[O:25])[C@@H:4]2[C@:21]3([CH3:22])[C@H:7]([C@H:8]4[C@H:18]([C:19](=[O:23])[CH2:20]3)[C@:16]3([CH3:17])[C@H:11]([CH2:12][C:13](=[O:24])[CH2:14][CH2:15]3)[CH2:10][CH2:9]4)[CH2:6][CH2:5]2)=[O:35])[CH2:28][CH2:27]1

Participants

4

Reactant 2

HCID 8673347421-Bromo-5alpha-pregnane-3,11,20-trioneHCID 178526202HCID 178526202, compound

Product 1

HCID 8673347521-Morpholinoacetylthio-5alpha-pregnane-3,11,20-trione

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

21-Bromo-5α-pregnane-3,11,20-trione (1.04 g.) was refluxed in dry acetone (100 ml) with morpholino thioacetic acid (600 mg) for 15 minutes. The reaction mixture was concentrated, partitioned between ethyl acetate, water, pH 8, the organic layer was washed, dried (MgSO4) and evaporated to an off white solid (1.26g.)

Workup

  1. concentrationThe reaction mixture was concentrated
  2. custompartitioned between ethyl acetate, water, pH 8
  3. washthe organic layer was washed
  4. dry with materialdried (MgSO4)
  5. customevaporated to an off white solid (1.26g.)

Sources & evidence

ORD record
ord-01fbc72acd6a4967b3bcd2a3737a6870
Source dataset
uspto-grants-1976_05
Patent number
US03959260

Reaction notes

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