Sodium Hydroxide → HCID 14080069, compound

HRID 840172Notes

Reaction equation

HRID 840172 reaction equation
C([O:4][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]([NH:15][C:16](=[O:24])[CH2:17][CH2:18]1)=[CH:13][CH2:12]3)(=O)C.C(O)C.O1CCCC1.[OH-].[Na+]>[Cl-].[Na+].O>[OH:4][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]([NH:15][C:16](=[O:24])[CH2:17][CH2:18]1)=[CH:13][CH2:12]3

Participants

5

Reactant 3

HCID 14798Sodium Hydroxide2×HCID 14521645HCID 14521645, compoundHCID 21873804Tetrahydrofuran ethanol

Product 1

HCID 14080069HCID 14080069, compoundYield 38.7%

Reagents, catalysts & solvents 1

HCID 57417360Sodium chloride; waterSolvent

Procedure

The 17β-ethyl carboxylate prepared in Example 1B (0.9259 g, 2.793 mmol) is dissolved in 60 mL warm ethanol/tetrahydrofuran (1:1), 6M sodium hydroxide is added (NaOH, 10.0 mL, 60 mmol) and the reaction is stirred at room temperature for 2 ½ hours. The reaction mixture is diluted with brine (100 mL) and extracted with EtOAc (3×50 mL). The combined organic phases are washed with brine (50 mL) and ammonium chloride (NH4Cl), dried over magnesium sulfate, filtered and evaporated to give a crude reaction product. The crude product is recrystallized from ethanol to give colorless crystals (0.3132 g, 1.0822 mmol) of 17β-hydroxy-4-aza-androst-5(6)-en-3-one. The mother liquor is concentrated and the recrystallization procedure above repeated in order to give a second crop of crystals. (0.3945 g, 1.363 mmole).

Workup

  1. extractionextracted with EtOAc (3×50 mL)
  2. washThe combined organic phases are washed with brine (50 mL) and ammonium chloride (NH4Cl)
  3. dry with materialdried over magnesium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customto give a crude
  7. customreaction product
  8. customThe crude product is recrystallized from ethanol

Sources & evidence

ORD record
ord-0f31f1d9d8e3448a96c2c4857d22ef87
Source dataset
uspto-grants-2002_04
Patent number
US06365597B1

Reaction notes

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