Dimethylformamide → HCID 22798533, compound

HRID 259156Notes

Reaction equation

HRID 259156 reaction equation
[CH3:1][Si:2]([CH3:37])([CH3:36])[O:3][C@H:4]1[CH2:27][C@@:26]2([CH3:28])[C@@H:15]([CH2:16][CH2:17][C@:18]2(OC(=O)C)[C:19](=[O:25])[CH2:20][O:21][C:22](=[O:24])[CH3:23])[C@H:14]2[C@@:5]1([F:35])[C@:6]1([CH3:34])[C@@H:11]([CH2:12][CH2:13]2)[CH2:10][C:9](=[O:33])[CH2:8][CH2:7]1.C([O-])(=O)C.[K+].CN(C)C=O>O>[CH3:37][Si:2]([CH3:1])([CH3:36])[O:3][C@H:4]1[CH2:27][C@@:26]2([CH3:28])[C@@H:15]([CH2:16][CH:17]=[C:18]2[C:19](=[O:25])[CH2:20][O:21][C:22](=[O:24])[CH3:23])[C@H:14]2[C@@:5]1([F:35])[C@:6]1([CH3:34])[C@@H:11]([CH2:12][CH2:13]2)[CH2:10][C:9](=[O:33])[CH2:8][CH2:7]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 517044Potassium AcetateHCID 2279852111beta-Trimethylsiloxy-17alpha,21-diacetoxy9alphafluoro-5alpha-pregnane3,20-dione

Product 1

HCID 22798533HCID 22798533, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 8.0 g of 11β-trimethylsiloxy-17α,21-diacetoxy9αfluoro-5α-pregnane3,20-dione obtained according to Example 19, 4 g anhydrous potassium acetate and 20 ml of dimethyl formamide was heated for a period of 4 hours at 110° -120° in an atmosphere of nitrogen. The reaction mixture was cooled and poured into 120 ml of water and ice. The mixture was left stirring for 30 minutes, then lft standing for a period of 2 hours, filtered, washed on the filter with abundant water, collected and dried. Trituration of this crude product with acetone/ether gave 11β-trimethylsiloxy-21-acetoxy-9α-fluoro-5α-pregn-16-ene-3,20-dione (compound 44). Yield: 7.0 g.

Workup

  1. customobtained
  2. temperaturewas heated for a period of 4 hours at 110° -120° in an atmosphere of nitrogen
  3. temperatureThe reaction mixture was cooled
  4. waitThe mixture was left
  5. waitlft standing for a period of 2 hours
  6. filtrationfiltered
  7. washwashed on the
  8. filtrationfilter with abundant water
  9. customcollected
  10. customdried

Sources & evidence

ORD record
ord-f934e256490847239476e1321b2584ff
Source dataset
uspto-grants-1977_07
Patent number
US04036831

Reaction notes

Loading…