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Hydrochloric Acid → (11beta,16beta)-9-Fluoro-11,21-dihydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl ethylcarbamate

HRID 14375
Notes
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Reaction equation

HRID 14375 reaction equation
[CH2:1]([NH:3][C:4](=[O:40])[O:5][C@:6]1([C@:30]2([CH3:31])[C@H:16]([C@H:17]3[C@:27]([F:37])([C@@H:28]([O:32][Si](C)(C)C)[CH2:29]2)[C@:25]2([CH3:26])[C:20](=[CH:21][C:22](=[O:38])[CH:23]=[CH:24]2)[CH2:19][CH2:18]3)[CH2:15][C@@H:14]1[CH3:39])[C:7](=[O:13])[CH2:8][O:9]C(=O)C)[CH3:2].Cl>CO.C(Cl)(Cl)Cl>[CH2:1]([NH:3][C:4](=[O:40])[O:5][C@:6]1([C@:30]2([CH3:31])[C@H:16]([C@H:17]3[C@:27]([F:37])([C@@H:28]([OH:32])[CH2:29]2)[C@:25]2([CH3:26])[C:20](=[CH:21][C:22](=[O:38])[CH:23]=[CH:24]2)[CH2:19][CH2:18]3)[CH2:15][C@@H:14]1[CH3:39])[C:7](=[O:13])[CH2:8][OH:9])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 68717367(11beta,16beta)-21-(Acetyloxy)-9-fluoro-16-methyl-3,20-dioxo-11-[(trimethylsilyl)-oxy]pregna-1,4-dien-17-yl ethylcarbamate

Product 1

HCID 9825650(11beta,16beta)-9-Fluoro-11,21-dihydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl ethylcarbamateYield 50%

Reagents, catalysts & solvents 1

HCID 21584188Chloroform methanol
Solvent

Procedure

Solid (11β,16β)-21-(acetyloxy)-9-fluoro-16-methyl-3,20-dioxo-11-[(trimethylsilyl)oxy]-pregna-1,4-dien-17-yl ethylcarbamate (2.22 g, 3.84 mmol) was dissolved in 128 mL of a pre-mixed solution of methanol/chloroform/6N HCl (10:2:1) and stirred at room temperature. After 16 hours, an additional 2 mL of 6N HCl was added. After 5 hours more, the solution was partitioned between ethyl acetate and water. The organic phase was washed successively with sat. NaHCO3, water, and brine. The organic layer was dried over Na2SO4, filtered and evaporated in vacuo to give a pale yellow oil. Purification by flash chromatography through a column of 500 g of silica gel, eluting with hexane/ethyl acetate/dichloromethane/methanol (3:3:3:1) yielded 0.890 g of (11β,16β)-9-fluoro-11,21-dihydroxy-16-methyl-3,20-dioxopregna-1,4-dien-17-yl ethylcarbamate as a white powder.

Workup

  1. waitAfter 5 hours more
  2. customthe solution was partitioned between ethyl acetate and water
  3. washThe organic phase was washed successively with sat. NaHCO3, water, and brine
  4. dry with materialThe organic layer was dried over Na2SO4
  5. filtrationfiltered
  6. customevaporated in vacuo
  7. customto give a pale yellow oil
  8. customPurification by flash chromatography through a column of 500 g of silica gel
  9. washeluting with hexane/ethyl acetate/dichloromethane/methanol (3:3:3:1)

Sources & evidence

ORD record
ord-158fe18b058341539cd1810757fda487
Source dataset
uspto-grants-2010_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07732432B2

Reaction notes

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