Water → 17beta-Carboxy-6-t-butoxycarbonyl-6-azaandrost-4-en-3-one

HRID 726133Notes

Reaction equation

HRID 726133 reaction equation
[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14](=[CH:15][C:16](=[O:24])[CH2:17][CH2:18]1)[N:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:12]3)([O:3]C)=[O:2].O.O[Li].O.OS([O-])(=O)=O.[Na+]>O1CCOCC1>[C:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]2[C@H:11]3[C@H:21]([CH2:22][CH2:23][C@:6]12[CH3:7])[C@:19]1([CH3:20])[C:14](=[CH:15][C:16](=[O:24])[CH2:17][CH2:18]1)[N:13]([C:25]([O:27][C:28]([CH3:31])([CH3:30])[CH3:29])=[O:26])[CH2:12]3)([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 516919Sodium BisulfateHCID 1000287217beta-Carbomethoxy-6-t-butoxycarbonyl-6-azaandrost-4-en-3-one

Product 1

HCID 1000204817beta-Carboxy-6-t-butoxycarbonyl-6-azaandrost-4-en-3-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 17β-carbomethoxy-6-t-butoxycarbonyl-6-azaandrost-4-en-3-one (15.4 g, 36 mmol), from part E, in dioxane (150 mL) and water (100 mL) is treated with LiOH.H2O (3.31 g, 79 mmol) and stirred overnight in a water bath. The reaction is poured into saturated aqueous NaHSO4 (150 mL), extracted with methylene chloride (3×100 mL), extracts washed with saturated aqueous NaCl, dried over MgSO4 and concentrated to a volume of 100 mL. At this point crystals begin to form and 2:1 hexanes/ethyl acetate (50 mL) is added, the mixture triturated, cooled to room temperature and 17β-carboxy-6-t-butoxycarbonyl-6-azaandrost-4-en-3-one collected as a fluffy white powder; yield: 9.44 g (63%); m.p. 215°-216° C. Anal. Calcd. for C24H35NO5.1/4H2O; C, 68.30; H, 8.48; N, 3.32. Found: C, 68.45; H, 8.41; N, 3.28.

Workup

  1. extractionextracted with methylene chloride (3×100 mL)
  2. washextracts washed with saturated aqueous NaCl
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated to a volume of 100 mL
  5. customto form
  6. customthe mixture triturated
  7. custom17β-carboxy-6-t-butoxycarbonyl-6-azaandrost-4-en-3-one collected as a fluffy white powder

Sources & evidence

ORD record
ord-35ceb399dcc7456b892caae04507d25f
Source dataset
uspto-grants-1998_01
Patent number
US05708001

Reaction notes

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