Potassium Carbonate → HCID 44587000, compound

HRID 14378Notes

Reaction equation

HRID 14378 reaction equation
[CH2:1]([NH:4][C:5](=[O:37])[O:6][C@:7]1([C@:31]2([CH3:32])[C@H:17]([C@H:18]3[C@:28]([F:34])([C@@H:29]([OH:33])[CH2:30]2)[C@:26]2([CH3:27])[C:21](=[CH:22][C:23](=[O:35])[CH:24]=[CH:25]2)[CH2:20][CH2:19]3)[CH2:16][C@@H:15]1[CH3:36])[C:8](=[O:14])[CH2:9][O:10]C(=O)C)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+]>O1CCCC1.CO.CO.O>[CH2:1]([NH:4][C:5](=[O:37])[O:6][C@:7]1([C@:31]2([CH3:32])[C@H:17]([C@H:18]3[C@:28]([F:34])([C@@H:29]([OH:33])[CH2:30]2)[C@:26]2([CH3:27])[C:21](=[CH:22][C:23](=[O:35])[CH:24]=[CH:25]2)[CH2:20][CH2:19]3)[CH2:16][C@@H:15]1[CH3:36])[C:8](=[O:14])[CH2:9][OH:10])[CH2:2][CH3:3]

Participants

6

Reactant 2

HCID 11430Potassium CarbonateHCID 68718109(11beta,16beta)-21-(Acetyloxy)-9-fluoro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl propylcarbamate

Product 1

HCID 44587000HCID 44587000, compoundYield 60.2%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolventHCID 22242641Methanol--water (1/1)Solvent

Procedure

To a solution of (11β,16β)-21-(acetyloxy)-9-fluoro-11-hydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl propylcarbamate (8.5 mg, 0.016 mmol) in 0.3 mL of tetrahydrofuran and 0.1 mL of methanol was added 0.030 mL of a 0.1M solution of potassium carbonate in methanol/water (9:1). After 10 minutes at room temperature, the solution was partitioned between ethyl acetate and water and the organic layer was washed with water (twice) and brine and dried over Na2SO4. The solution was filtered and evaporated in vacuo to give an oil which was purified by preparative thin layer chromatography on silica gel, eluting with ethyl acetate/hexane/dichloromethane/methanol (3:3:3:1), to yield 4.6 mg of the title compound as a semi-solid.

Workup

  1. customthe solution was partitioned between ethyl acetate and water
  2. washthe organic layer was washed with water (twice) and brine
  3. dry with materialdried over Na2SO4
  4. filtrationThe solution was filtered
  5. customevaporated in vacuo
  6. customto give an oil which
  7. customwas purified by preparative thin layer chromatography on silica gel
  8. washeluting with ethyl acetate/hexane/dichloromethane/methanol (3:3:3:1)

Sources & evidence

ORD record
ord-745cb2f268514ca79e1840febacbaeba
Source dataset
uspto-grants-2010_06
Patent number
US07732432B2

Reaction notes

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