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

HRID 1077589Notes

Reaction equation

HRID 1077589 reaction equation
[C:1]([C@H:5]1[CH2:13][CH2:12][C@H:11]2[C@H:14]3[C@H:24]([CH2:25][CH2:26][C@:6]12[CH2:7][C:8]([OH:10])=[O:9])[C@:22]1([CH3:23])[C:17](=[CH:18][C:19](=[O:27])[CH2:20][CH2:21]1)[N:16]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:15]3)([O:3]C)=[O:2].O.O[Li].O.OS([O-])(=O)=O.[Na+]>O1CCOCC1>[C:1]([C@H:5]1[CH2:13][CH2:12][C@H:11]2[C@H:14]3[C@H:24]([CH2:25][CH2:26][C@:6]12[CH2:7][C:8]([OH:10])=[O:9])[C@:22]1([CH3:23])[C:17](=[CH:18][C:19](=[O:27])[CH2:20][CH2:21]1)[N:16]([C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:15]3)([OH:3])=[O:2]

Participants

6

Reactant 4

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 516919Sodium BisulfateHCID 8674903517beta-Carbomethoxy-6-t-butylcarboxy-6-azaandrost-4-en-3-one

Product 1

HCID 8674903417beta-Carboxy-6-t-butylcarboxy-6-azaandrost-4-en-3-one

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 17β-carbomethoxy-6-t-butylcarboxy-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 on 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-butylcarboxy-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-butylcarboxy-6-azaandrost-4-en-3-one collected as a fluffy white powder

Sources & evidence

ORD record
ord-e303bbe3491945168c7a5fbe38e788f0
Source dataset
uspto-grants-1996_08
Patent number
US05543406

Reaction notes

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