Methyl iodide → HCID 22875674, compound

HRID 2258016Notes

Reaction equation

HRID 2258016 reaction equation
[CH3:1][C@H:2]1[CH2:23][C@@H:22]2[C@:17]([CH3:25])([CH:18]=[CH:19][C:20](=[O:24])[NH:21]2)[C@@H:16]2[C@@H:3]1[C@H:4]1[C@:13]([CH3:26])([CH2:14][CH2:15]2)[C@@H:7]([C@:8]([CH2:11][CH3:12])([OH:10])[CH3:9])[CH2:6][CH2:5]1.[CH3:27]I.[H-].[Na+].[Cl-].[NH4+]>CN(C)C=O.O>[CH3:27][N:21]1[C:20](=[O:24])[CH:19]=[CH:18][C@@:17]2([CH3:25])[C@H:22]1[CH2:23][C@H:2]([CH3:1])[C@@H:3]1[C@@H:16]2[CH2:15][CH2:14][C@@:13]2([CH3:26])[C@H:4]1[CH2:5][CH2:6][C@@H:7]2[C@:8]([CH2:11][CH3:12])([OH:10])[CH3:9]

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 22875677HCID 22875677, compound

Product 1

HCID 22875674HCID 22875674, compoundYield 63%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 46 mg (0.128 mmol) of 7β-methyl-20-ethyl-20(S)-hydroxy-5α-4-azapregn-1-en-3-one (from Example 6) in 5 ml dry dimethylformamide was cooled to 0° C. under N2. Methyl iodide (10 eq, 1.3 mmol) and sodium hydride (2 eq, 25 mmol) were added and the reaction was stirred at RT for 24 hours. Aqueous ammonium chloride was added and the reaction mixture was poured onto 100 ml water and extracted with three 25 ml portions of ethyl acetate. The organic layer was washed with water, brine, dried over magnesium sulfate, and evaporated. The product was purified by silica gel MPLC using 10% acetone/methylene chloride to yield 30 mg (0.08 mmol, 63% yield) of the title compound.

Workup

  1. extractionextracted with three 25 ml portions of ethyl acetate
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe product was purified by silica gel MPLC

Sources & evidence

ORD record
ord-805f4aad6aa844ee863c941475e2bfa7
Source dataset
uspto-grants-1997_08
Patent number
US05658922

Reaction notes

Loading…