Water → HCID 9932026, compound

HRID 2292494Notes

Reaction equation

HRID 2292494 reaction equation
Cl([O-])=O.[Na+].[F:5][C:6]1[CH:34]=[CH:33][C:9]([C:10]([C@H:12]2[CH2:17][CH2:16][C@H:15]3[C@H:18]4[C@H:28]([CH2:29][CH2:30][C@:13]23[CH3:14])[C@:26]2([CH3:27])[C:21]([CH:22]=[C:23]([CH:31]=[O:32])[CH2:24][CH2:25]2)=[CH:20][CH2:19]4)=[O:11])=[CH:8][CH:7]=1.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]1[CH:7]=[CH:8][C:9]([C:10]([C@H:12]2[CH2:17][CH2:16][C@H:15]3[C@H:18]4[C@H:28]([CH2:29][CH2:30][C@:13]23[CH3:14])[C@:26]2([CH3:27])[C:21]([CH:22]=[C:23]([C:31]([OH:36])=[O:32])[CH2:24][CH2:25]2)=[CH:20][CH2:19]4)=[O:11])=[CH:33][CH:34]=1

Participants

9

Reactant 4

HCID 962WaterHCID 24243Trisodium PhosphateHCID 23668197Sodium ChloriteHCID 54571409HCID 54571409, compound

Product 1

HCID 9932026HCID 9932026, compound

Reagents, catalysts & solvents 4

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

Procedure

Sodium chlorite is added to a mixture of 17β-(4-fluorobenzoyl)-androsta-3,5-diene-3-carboxaldehyde, sodium phosphate, monobasic monohydrate in 2-methyl-2-butene in THF, H2O, and t-butanol at RT. After 6 h acetic acid was added, then the aqueous layer is extracted with EtOAc, the combined organic extracts are dried (MgSO4), filtered, concentrated, and flash chromatographed to yield the title compound.

Workup

  1. customat RT
  2. extractionthe aqueous layer is extracted with EtOAc
  3. dry with materialthe combined organic extracts are dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customflash chromatographed

Sources & evidence

ORD record
ord-b2c1cb349a34487c93452157e22a20ca
Source dataset
uspto-grants-1997_11
Patent number
US05683995

Reaction notes

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