Hydrochloric Acid → HCID 10193144, compound

HRID 855479Notes

Reaction equation

HRID 855479 reaction equation
F[C:2]([F:17])(S(F)(=O)=O)[C:3](F)(F)[C:4](F)(F)[C:5](F)(F)F.O[C@@H]1C[C@@]2(C)[C@@H:30]([CH2:31][CH2:32][C:33]2=[O:37])[C@H:29]2[C@H:20]1[C@@H:21]1[C:26]([CH2:27][C@H:28]2[CH3:38])=[CH:25][C:24](=[O:39])[CH2:23][CH2:22]1.Cl.O>C1(C)C=CC=CC=1.N12CCCN=C1CCCCC2>[F:17][C@H:2]1[CH2:3][C@@:4]2([CH3:5])[C@@H:30]([CH2:31][CH2:32][C:33]2=[O:37])[C@H:29]2[C@H:20]1[C@@H:21]1[C:26]([CH2:27][C@H:28]2[CH3:38])=[CH:25][C:24](=[O:39])[CH2:23][CH2:22]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 67814Perfluoro-1-butanesulfonyl fluorideHCID 1202027311alpha-Hydroxy-7alpha-methylestr-4-ene-3,17-dione

Product 1

HCID 10193144HCID 10193144, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneSolvent

Procedure

11.5 ml of perfluorobutane-1-sulfonic acid fluoride was added in drops at 0° C. to a solution of 13.08 g of 11α-hydroxy-7α-methyl-estr-4-ene-3,17-dione (produced by means of microbiological synthesis according to the invention [Part A]) in 250 ml of toluene and 18.2 ml of 1,8-diazabicyclo[5,4,0]undec-7-ene. After 1 hour, it was neutralized with 2 M hydrochloric acid, added to water, extracted four times with ethyl acetate, washed with saturated sodium chloride solution, dried and concentrated by evaporation in a vacuum. After the crude product was chromatographed on silica gel with a hexane/ethyl acetate gradient, 8.7 g of 11β-fluoro-7α-methyl-estr-4-ene-3,17-dione was obtained. Melting point: 101.4° C., [α]D: +135.8° (CHCl3).

Workup

  1. customproduced by means of microbiological synthesis
  2. extractionextracted four times with ethyl acetate
  3. washwashed with saturated sodium chloride solution
  4. customdried
  5. concentrationconcentrated by evaporation in a vacuum
  6. customAfter the crude product was chromatographed on silica gel with a hexane/ethyl acetate gradient

Sources & evidence

ORD record
ord-348b1f529ae34e0cbca1eabc2ccb7f14
Source dataset
uspto-grants-2007_08
Patent number
US07262023B2

Reaction notes

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