HCID 13375774, compound → HCID 70400268, compound

HRID 371059Notes

Reaction equation

HRID 371059 reaction equation
C([O:4][C@H:5]1[CH2:22][C@@:20]2([CH3:21])[C@@H:16]([CH2:17][CH2:18][C@@H:19]2[S:23][CH3:24])[C@H:15]2[C@@:6]1([F:27])[C@:7]1([CH3:26])[C:12]([CH2:13][CH2:14]2)=[CH:11][C:10](=[O:25])[CH:9]=[CH:8]1)(=O)C>CO.O1CCCC1>[F:27][C@:6]12[C@@H:5]([OH:4])[CH2:22][C@@:20]3([CH3:21])[C@@H:16]([CH2:17][CH2:18][C@@H:19]3[S:23][CH3:24])[C@@H:15]1[CH2:14][CH2:13][C:12]1[C@:7]2([CH3:26])[CH:8]=[CH:9][C:10](=[O:25])[CH:11]=1

Participants

4

Reactant 1

HCID 13375774HCID 13375774, compound

Product 1

HCID 70400268HCID 70400268, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of (11β,17β)-11-(acetyloxy)-9-fluoro-17-(methylthio)androsta-1,4-dien-3-one (2.0 g; 5.09 mmole) in a mixture of methanol (15 ml) and tetrahydrofuran (15 ml) was flushed well with nitrogen, 3M aqueous sodium hydroxide (2.0 ml) was added and the mixture was stirred at room temperature for 45 minutes. A moderate excess of acetic acid was added, the mixture was concentrated in vacuo and was diluted with water. The steroid that separated was isolated by filtration, washed with water, dried, crystallized from ethyl acetate-hexane and dried (100° C., 0.3 mm of Hg, 10 hours) to afford the homogeneous (tlc) analytical specimen of the title commpound (1.4 g), melting point 269°-270° C. with consistent spectral data.

Workup

  1. customwas flushed well with nitrogen, 3M aqueous sodium hydroxide (2.0 ml)
  2. additionwas added
  3. additionA moderate excess of acetic acid was added
  4. concentrationthe mixture was concentrated in vacuo
  5. additionwas diluted with water
  6. customThe steroid that separated
  7. customwas isolated by filtration
  8. washwashed with water
  9. customdried
  10. customcrystallized from ethyl acetate-hexane
  11. customdried (100° C., 0.3 mm of Hg, 10 hours)
  12. customto afford the homogeneous (tlc) analytical specimen of the title commpound (1.4 g), melting point 269°-270° C. with consistent spectral data

Sources & evidence

ORD record
ord-856c7e874c0641c1aba610e2af09bbbc
Source dataset
uspto-grants-1985_07
Patent number
US04529548

Reaction notes

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