Sodium Acetate → HCID 70626861, compound

HRID 1763850Notes

Reaction equation

HRID 1763850 reaction equation
[F:1][C@:2]12[C@@H:21]([OH:22])[CH2:20][C@@:19]3([CH3:23])[C@@H:12]([CH2:13][CH:14]=[C:15]3[C:16](=[O:18])[CH3:17])[C@@H:11]1[CH2:10][CH2:9][C:8]1[C@:3]2([CH3:25])[CH:4]=[CH:5][C:6](=[O:24])[CH:7]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:38]([O-])(=[O:40])[CH3:39].[Na+]>C(O)(=O)C.C(OC(=O)C)(=O)C>[C:38]([O:22][C@H:21]1[CH2:20][C@@:19]2([CH3:23])[C@@H:12]([CH2:13][CH:14]=[C:15]2[C:16](=[O:18])[CH3:17])[C@H:11]2[C@@:2]1([F:1])[C@:3]1([CH3:25])[C:8]([CH2:9][CH2:10]2)=[CH:7][C:6](=[O:24])[CH:5]=[CH:4]1)(=[O:40])[CH3:39]

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 521998p-Toluenesulfonic acid monohydrateHCID 70626946HCID 70626946, compound

Product 1

HCID 70626861HCID 70626861, compoundYield 80.2%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 7918Acetic AnhydrideSolvent

Procedure

A solution of 9-fluoro-11β-hydroxypregna-1,4,16-triene-3,20-dione (1.0g) in a mixture of acetic acid (70 ml) and acetic anhydride (70 ml) containing p-toluenesulfonic acid hydrate (500 mg) is stirred at room temperature for 60 hours. Sodium acetate (2.0g) is added and the mixture is concentrated in vacuo. The residue is mixed with water and washed with a dilute sodium bicarbonate solution and water, dried and the residue is crystallized from ethyl acetate-hexane to afford 0.9g of the title compound, melting point 202°-203° C.

Workup

  1. concentrationthe mixture is concentrated in vacuo
  2. additionThe residue is mixed with water
  3. washwashed with a dilute sodium bicarbonate solution and water
  4. customdried
  5. customthe residue is crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-03905aa5dd474c888fc7a93556bda756
Source dataset
uspto-grants-1978_09
Patent number
US04113722

Reaction notes

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