HCID 86733743, compound → HCID 68128669, compound

HRID 918378Notes

Reaction equation

HRID 918378 reaction equation
[F:1][C@:2]12[C@@H:22]([OH:23])[CH2:21][C@@:20]3([CH3:24])[C@@H:12]([CH2:13][C@@H:14]([O:26][CH2:27][CH2:28][O:29]C4CCCCO4)[C@:15]3([OH:25])[C:16](=[O:19])[CH2:17][OH:18])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:37])[CH2:4][CH2:5][C:6](=[O:36])[CH:7]=1>C(O)(=O)C.O>[F:1][C@:2]12[C@@H:22]([OH:23])[CH2:21][C@@:20]3([CH3:24])[C@@H:12]([CH2:13][C@@H:14]([O:26][CH2:27][CH2:28][OH:29])[C@:15]3([OH:25])[C:16](=[O:19])[CH2:17][OH:18])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:37])[CH2:4][CH2:5][C:6](=[O:36])[CH:7]=1

Participants

4

Reactant 1

HCID 86733743HCID 86733743, compound

Product 1

HCID 68128669HCID 68128669, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A solution of 4.4 g of 9-fluoro-11β,17,21-trihydroxy-16α-[2-(tetrahydropyran-2-yloxy)ethoxy]pregn-4-ene-3,20-dione, 21-acetate in 60 ml each of acetic acid and water is stirred for 4 hours and the bulk of the solvent removed in vacuo. The residue is dissolved in chloroform and washed with 5% sodium bicarbonate solution. Drying and solvent removal gives an oil which crystallizes from acetone-hexane to give 2.4 g of 9-fluoro-11β,17,21-trihydroxy-16α-(2-hydroxyethoxy)pregn-4-ene-3,20-dione, 21-acetate, melting point 162°-165°C.

Workup

  1. customthe bulk of the solvent removed in vacuo
  2. dissolutionThe residue is dissolved in chloroform
  3. washwashed with 5% sodium bicarbonate solution
  4. customDrying
  5. customsolvent removal
  6. customgives an oil which
  7. customcrystallizes from acetone-hexane

Sources & evidence

ORD record
ord-30f0f7478d204e149e03bf82f32cbdcc
Source dataset
uspto-grants-1976_07
Patent number
US03971772

Reaction notes

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