Sodium Hydroxide → HCID 15838319, compound

HRID 1735159Notes

Reaction equation

HRID 1735159 reaction equation
[CH3:1][N:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[C@H:3]1[CH2:4][CH2:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[O:22][CH2:23][C:24]([O:26]CC)=[O:25].[OH-].[Na+]>C1COCC1.CO>[CH3:1][N:2]1[C:19](=[O:20])[CH2:18][CH2:17][C@@:16]2([CH3:21])[C@H:3]1[CH2:4][CH2:5][C@@H:6]1[C@@H:15]2[CH2:14][CH2:13][C@@:11]2([CH3:12])[C@H:7]1[CH2:8][CH2:9][C@@H:10]2[O:22][CH2:23][C:24]([OH:26])=[O:25]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 15838329HCID 15838329, compound

Product 1

HCID 15838319HCID 15838319, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To ethyl 4-methyl-5α-4-azaandrostan-3-on-17β-yloxyacetate (275 mg) in THF (10 ml) and MeOH (5 ml) under N2 was added 2N NaOH (3.0 ml). The mixture was stirred at room temperature for 2 hours, then concentrated in vacuo. The aqueous residue was extracted with CH2Cl2. The aqueous layer was then acidified with 3.0 N HCl (ca. 2.1 ml) to pH 2, and extracted with CH2Cl2. The organic layer was washed with brine and dried (Na2SO4). The solvent was removed, and the crude product recrystallized from CH2Cl2 /hexane to give the title compound. m.p. 180.5°-184° C.

Workup

  1. concentrationconcentrated in vacuo
  2. extractionThe aqueous residue was extracted with CH2Cl2
  3. extractionextracted with CH2Cl2
  4. washThe organic layer was washed with brine
  5. dry with materialdried (Na2SO4)
  6. customThe solvent was removed
  7. customthe crude product recrystallized from CH2Cl2 /hexane

Sources & evidence

ORD record
ord-79181817961244d3a96503a07eab40dd
Source dataset
uspto-grants-1996_07
Patent number
US05536727

Reaction notes

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