Acetic Acid → HCID 22798537, compound

HRID 259157Notes

Reaction equation

HRID 259157 reaction equation
[OH:1][C@:2]1([C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@:23]([F:33])([C@@H:24]([O:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:34])[CH:19]=[CH:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[C:3](=[O:9])[CH2:4][O:5][C:6](=[O:8])[CH3:7].ClCCl.[C:38](O)(=[O:40])[CH3:39].FC(F)(F)C(OC(=O)C(F)(F)F)=O>CC(CC(C)C)=O>[C:38]([O:1][C@:2]1([C@:26]2([CH3:27])[C@H:12]([C@H:13]3[C@:23]([F:33])([C@@H:24]([O:28][Si:29]([CH3:31])([CH3:30])[CH3:32])[CH2:25]2)[C@:21]2([CH3:22])[C:16](=[CH:17][C:18](=[O:34])[CH:19]=[CH:20]2)[CH2:15][CH2:14]3)[CH2:11][CH2:10]1)[C:3](=[O:9])[CH2:4][O:5][C:6](=[O:8])[CH3:7])(=[O:40])[CH3:39]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 6344DichloromethaneHCID 9845Trifluoroacetic anhydrideHCID 22798538HCID 22798538, compound

Product 1

HCID 22798537HCID 22798537, compound

Reagents, catalysts & solvents 1

HCID 7909Methyl Isobutyl KetoneSolvent

Procedure

A mixture of the 17α-hydroxy-21-acetoxy-11β-trimethylsiloxy-9α-fluoro-pregn-1,4-diene-3,20-dione from Example 26 (20.6 g) dichloromethane (50 ml) and acetic acid (20 ml) was treated with trifluoro-acetic anhydride (20 ml) for a period of 5 hours at 25°. The reaction mixture was diluted with methyl-isobutylketone (200 ml) and extracted with sodium bicarbonate solution (500 ml) and then with water (200 ml). The organic layer was dried over sodium sulfate, and evaporated to dryness under reduced pressure. The residue was amorphous, homogenous in TLC (BPB, silica plates No. 254). Crystalline 17α,21-diacetoxy-11β-trimethylsiloxy-9α-fluoropregna-1,4-diene-3,20 -dione (compound 53) was obtained directly from the residue by trituration with methanol.

Workup

  1. extractionextracted with sodium bicarbonate solution (500 ml)
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-03da9c9978bb4806b3451b2a6e01fcee
Source dataset
uspto-grants-1977_07
Patent number
US04036831

Reaction notes

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