Water → 7alpha-(5-Acetoxypentyl)-11beta-fluorooestr-4-ene-3,17-dione

HRID 1838881Notes

Reaction equation

HRID 1838881 reaction equation
[F:1][C@H:2]1[CH2:19][C@@:17]2([CH3:18])[C@@H:13]([CH2:14][CH2:15][C:16]2=[O:20])[C@H:12]2[C@H:3]1[C@@H:4]1[C:9]([CH2:10][C@H:11]2[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][OH:26])=[CH:8][C:7](=[O:27])[CH2:6][CH2:5]1.[C:28](OC(=O)C)(=[O:30])[CH3:29].O>N1C=CC=CC=1>[C:28]([O:26][CH2:25][CH2:24][CH2:23][CH2:22][CH2:21][C@@H:11]1[CH2:10][C:9]2[C@H:4]([CH2:5][CH2:6][C:7](=[O:27])[CH:8]=2)[C@@H:3]2[C@@H:12]1[C@H:13]1[C@@:17]([CH2:19][C@@H:2]2[F:1])([CH3:18])[C:16](=[O:20])[CH2:15][CH2:14]1)(=[O:30])[CH3:29]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 1587066111beta-Fluoro-7alpha-(5-hydroxypentyl)-estr4-ene-3,17-dione

Product 1

HCID 699353277alpha-(5-Acetoxypentyl)-11beta-fluorooestr-4-ene-3,17-dione

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

20 g of 11β-fluoro-7α-(5-hydroxypentyl)oestr-4-ene-3,17-dione in 100 ml of pyridine are allowed to react at 25° C. for 2 h with 50 ml of acetic anhydride. 5 ml of water are then added at 0° C. and the mixture is stirred for 45 min. It is extracted with diethyl ether, washed with 2N sulphuric acid until free of pyridine and neutralized successively with saturated sodium hydrogencarbonate solution and water. After drying and concentrating in vacuo, the crude product is chromatographed on silica gel using a hexane-ethyl acetate gradient. 17 g of 7α-(5-acetoxypentyl)-11β-fluorooestr-4-ene-3,17-dione of melting point 78.4° C. are obtained.

Workup

  1. extractionIt is extracted with diethyl ether
  2. washwashed with 2N sulphuric acid until free of pyridine
  3. customAfter drying
  4. concentrationconcentrating in vacuo
  5. customthe crude product is chromatographed on silica gel using a hexane-ethyl acetate gradient

Sources & evidence

ORD record
ord-b2447d696b5a4d44952c1cf3d215ee1e
Source dataset
uspto-grants-2004_01
Patent number
US06677324B1

Reaction notes

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