Water → HCID 9937514, compound

HRID 1744795Notes

Reaction equation

HRID 1744795 reaction equation
[Si]([O:8][C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:10]12[CH3:11])[C@:23]1([CH3:24])[C@H:18]([CH2:19][C:20](=[O:28])[CH2:21][CH2:22]1)[CH2:17][C@H:16]3[CH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[C:36]([O:38][CH2:39][CH2:40][CH2:41][C:42]([N:44]([CH3:46])[CH3:45])=[O:43])[CH:35]=[C:34]([OH:47])[CH:33]=1)(C(C)(C)C)(C)C.O>CC(C)=O.Cl>[OH:8][C@H:9]1[CH2:14][CH2:13][C@H:12]2[C@H:15]3[C@H:25]([CH2:26][CH2:27][C@:10]12[CH3:11])[C@:23]1([CH3:24])[C@H:18]([CH2:19][C:20](=[O:28])[CH2:21][CH2:22]1)[CH2:17][C@H:16]3[CH2:29][CH2:30][CH2:31][C:32]1[CH:37]=[C:36]([O:38][CH2:39][CH2:40][CH2:41][C:42]([N:44]([CH3:46])[CH3:45])=[O:43])[CH:35]=[C:34]([OH:47])[CH:33]=1

Participants

5

Reactant 2

HCID 962WaterHCID 10233461HCID 10233461, compound

Product 1

HCID 9937514HCID 9937514, compoundYield 65.3%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 313Hydrochloric AcidSolvent

Procedure

To a solution of 17β-(tert-butyldimethylsilyloxy)-7α-(3-(3-hydroxy-5-(3-(N,N-dimethylaminocarbonyl)propoxy)phenyl)propyl)-5α-androstan-3-one (12.0 mg) in acetone (1 ml), 2N hydrochloric acid (1 ml) was added at 25° C. and stirred for 35 minutes. Water was added to the reaction mixture, which was then extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride, dried over anhydrous magnesium sulfate and then filtered. After evaporation under reduced pressure to remove the solvent, the resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate) to give 17β-hydroxy-7α-(3-(3-hydroxy-5-(3-(N,N-dimethylaminocarbonyl)propoxy)phenyl)propyl)-5α-androstan-3-one (6.5 mg, yield 65%).

Workup

  1. extractionwas then extracted with ethyl acetate
  2. washThe organic layer was washed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customAfter evaporation under reduced pressure
  6. customto remove the solvent
  7. customthe resulting residue was purified by silica gel column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-817ff73d3f3c49afaf031ae1104fc57b
Source dataset
uspto-grants-2006_03
Patent number
US07018993B2

Reaction notes

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