Dimethylformamide → HCID 22842293, compound

HRID 1681300Notes

Reaction equation

HRID 1681300 reaction equation
C([O:5][C:6](=[C:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C:23](=[CH:24][CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[CH:7]=[O:8])(=O)CC.[C:29]([O-:32])(=O)[CH3:30].[K+].[CH3:34]N(C)C=O>>[C:29]([O:8][CH2:7][C:6](=[O:5])[C:9]1[C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C:23](=[CH:24][CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:28])[CH2:19][CH2:20]2)[CH2:15][CH2:14]3)[CH2:11][CH:10]=1)(=[O:32])[CH2:30][CH3:34]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 517044Potassium AcetateHCID 57025548HCID 57025548, compound

Product 1

HCID 22842293HCID 22842293, compoundYield 78.2%

Procedure

Into a reactor were charged 0.2 m mole of the 20-propionyloxy-3-oxo-pregna-4,9(11),17(20)-trien-21-al obtained in Example 10, 0.3 m mole of potassium acetate and 2 ml of dimethylformamide, and stirred under nitrogen at room temperature for 2 days. Then, the resulting mixture was heated to 50% and stirred for 10 hours. After completion of the reaction, the reaction mixture was treated in the same manner as in Referential Example 1 to obtain 21-propionyloxy-pregna-4,9(11),16-triene-3,20-dione of the following structural formula in 78.2% yield: ##STR42##

Workup

  1. temperatureThen, the resulting mixture was heated to 50%
  2. stirringstirred for 10 hours
  3. customAfter completion of the reaction
  4. additionthe reaction mixture was treated in the same manner as in Referential Example 1

Sources & evidence

ORD record
ord-1e731faf0dc841a09f8806411e223787
Source dataset
uspto-grants-1992_12
Patent number
US05169966

Reaction notes

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