Hydrochloric Acid → HCID 59526504, compound

HRID 2197394Notes

Reaction equation

HRID 2197394 reaction equation
C(OC[C:6]([C@:8]1([OH:30])[C@:24]2([CH3:25])[C@H:11]([C@H:12]3[C@:21]([F:27])([C@@H:22]([OH:26])[CH2:23]2)[C@:20]2([CH3:28])[C:15](=[CH:16][C:17](=[O:29])[CH2:18][CH2:19]2)[CH2:14][CH2:13]3)[CH2:10][CH2:9]1)=[O:7])(=O)C.[OH-].[Na+].Cl.I(O)(O)(O)(O)(O)=[O:35]>CO.O>[F:27][C@@:21]12[C@:20]3([CH3:28])[C:15](=[CH:16][C:17](=[O:29])[CH2:18][CH2:19]3)[CH2:14][CH2:13][C@H:12]1[C@H:11]1[C@@:24]([CH3:25])([C@@:8]([OH:30])([C:6]([OH:35])=[O:7])[CH2:9][CH2:10]1)[CH2:23][C@@H:22]2[OH:26]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 25289Orthoperiodic acidHCID 225609Fludrocortisone Acetate

Product 1

HCID 59526504HCID 59526504, compoundYield 101.1%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent2×

Procedure

In a 1000 mL round-bottomed flask was suspended 2-((8S,9R,10S,11S,13S,14S,17R)-9-fluoro-11,17-dihydroxy-10,13-dimethyl-3-oxo-2,3,6,7,8,9,10,11,12,13,14,15,16,17-tetradecahydro-1H-cyclopenta[a]phenanthren-17-yl)-2-oxoethyl acetate (Fludrocortisone-21-acetate, 22.8 g, 53.97 mmol) in MeOH (200 mL) and the suspension was degassed with nitrogen. 2M sodium hydroxide (40.5 mL, 80.95 mmol) was added to the solution and the mixture was stirred for 10 minutes. To the solution was added 4M HCl (20 ml, 80 mmol) and MeOH was removed in vacuo. The obtained residue was dissolved in THF (200 ml), a solution of orthoperiodic acid (15.99 g, 70.16 mmol) in water (40 ml) was added at room temperature and the obtained mixture was stirred for 1 hour. 100 ml of water was added and the organic solvent was removed in vacuo. An additional 100 ml of water was added to the aqueous residue and the obtained solid was collected by filtration, was washed with water (2×200 ml) and was air dried on the sinter, followed by drying in vacuo to yield 20 g of the desired compound as an off-white solid. APCI-MS m/z: 367 [MH+].

Workup

  1. customIn a 1000 mL round-bottomed flask was suspended
  2. customwas removed in vacuo
  3. dissolutionThe obtained residue was dissolved in THF (200 ml)
  4. stirringthe obtained mixture was stirred for 1 hour
  5. customthe organic solvent was removed in vacuo
  6. additionAn additional 100 ml of water was added to the aqueous residue
  7. filtrationthe obtained solid was collected by filtration
  8. washwas washed with water (2×200 ml)
  9. customdried on the sinter
  10. customby drying in vacuo

Sources & evidence

ORD record
ord-6b70c65fe80b4eb8b47b41ce86d01cf3
Source dataset
uspto-grants-2012_12
Patent number
US08338587B2

Reaction notes

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