Water → HCID 53711472, compound

HRID 1684567Notes

Reaction equation

HRID 1684567 reaction equation
Cl([O-])=O.[Na+].[F:5][C:6]([F:34])([F:33])[CH2:7][CH2:8][CH2:9][C:10]([C@H:12]1[CH2:17][CH2:16][C@H:15]2[C@H:18]3[C@H:28]([CH2:29][CH2:30][C@:13]12[CH3:14])[C@:26]1([CH3:27])[C:21]([CH:22]=[C:23]([CH:31]=[O:32])[CH2:24][CH2:25]1)=[CH:20][CH2:19]3)=[O:11].P([O-])([O-])([O-])=[O:36].[Na+].[Na+].[Na+].O>CC(=CC)C.C1COCC1.C(O)(=O)C.C(O)(C)(C)C>[F:5][C:6]([F:33])([F:34])[CH2:7][CH2:8][CH2:9][C:10]([C@H:12]1[CH2:17][CH2:16][C@H:15]2[C@H:18]3[C@H:28]([CH2:29][CH2:30][C@:13]12[CH3:14])[C@:26]1([CH3:27])[C:21]([CH:22]=[C:23]([C:31]([OH:36])=[O:32])[CH2:24][CH2:25]1)=[CH:20][CH2:19]3)=[O:11]

Participants

9

Reactant 4

HCID 962WaterHCID 24243Trisodium PhosphateHCID 22874155HCID 22874155, compoundHCID 23668197Sodium Chlorite

Product 1

HCID 53711472HCID 53711472, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 6386tert-ButanolSolventHCID 8028TetrahydrofuranSolventHCID 105532-Methyl-2-buteneSolvent

Procedure

Sodium chlorite (53 mg, 0.6 mmol) was added to a mixture of 17β-(5,5,5-trifluoro-1-oxopentyl)-androsta-3,5-diene-3-carboxaldehyde (50 mg, 0.12 mmol), sodium phosphate, monobasic monohydrate (140 mg, 1.18 mmol) in 2-methyl-2-butene in THF (2.0M, 3.0 ml), H2O (0.5 mL), and t-butanol (0.5 ml) at RT. After 6 h acetic acid (3.0 mL) was added, then the aqueous layer was extracted with EtOAc (10 mL), the combined organic extracts were dried (MgSO4), filtered, concentrated, and flash chromatographed (silica gel, 1% AcOH/19% EtOAc/80% hexanes) to yield the title compound as a white waxy solid. ESMS m/e 439 [M+H]+

Workup

  1. customat RT
  2. extractionthe aqueous layer was extracted with EtOAc (10 mL)
  3. dry with materialthe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customflash chromatographed (silica gel, 1% AcOH/19% EtOAc/80% hexanes)

Sources & evidence

ORD record
ord-f4de43ed66cd41a180881bcacaca84e4
Source dataset
uspto-grants-1997_06
Patent number
US05641765

Reaction notes

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