Ammonium Chloride → HCID 22875677, compound

HRID 2258015Notes

Reaction equation

HRID 2258015 reaction equation
[CH3:1][C@H:2]1[CH2:21][C@@H:20]2[C@:15]([CH3:23])([CH:16]=[CH:17][C:18](=[O:22])[NH:19]2)[C@@H:14]2[C@@H:3]1[C@H:4]1[C@:11]([CH3:24])([CH2:12][CH2:13]2)[C@@H:7]([C:8](=[O:10])[CH3:9])[CH2:6][CH2:5]1.[CH2:25]([Mg]Br)[CH3:26].[Cl-].[NH4+]>O1CCCC1.CCOCC>[CH3:1][C@H:2]1[CH2:21][C@@H:20]2[C@:15]([CH3:23])([CH:16]=[CH:17][C:18](=[O:22])[NH:19]2)[C@@H:14]2[C@@H:3]1[C@H:4]1[C@:11]([CH3:24])([CH2:12][CH2:13]2)[C@@H:7]([C@:8]([CH2:25][CH3:26])([OH:10])[CH3:9])[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 22875684HCID 22875684, compoundHCID 178418443HCID 178418443, compound

Product 1

HCID 22875677HCID 22875677, compoundYield 49%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 100 mg (0.303 mmol) 7β-methyl-5α-4-azapregn-1-ene-3,20-dione in 10 ml dry tetrahydrofuran at -40° C. under N2 was added 15 eq ethylmagnesium bromide (4.5 mmol) in ether. The reaction was stirred and allowed to warm to RT over 18 hours. Aqueous ammonium chloride (5 ml) was added and the solvents were evaporated. The residue was partitioned between methylene chloride and water. The organic layer was washed with brine, dried over magnesium sulfate, and evaporated. The product was purified via HPLC on a 19×300 mm 8 micron silica column using 5% isopropanol/hexane at 20 ml/min to yield 53 mg (0.147 mmol, 49% yield) of the title compound.

Workup

  1. customthe solvents were evaporated
  2. customThe residue was partitioned between methylene chloride and water
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe product was purified via HPLC on a 19×300 mm 8 micron silica column

Sources & evidence

ORD record
ord-d837f9a0476c4a709be73e0850929556
Source dataset
uspto-grants-1997_08
Patent number
US05658922

Reaction notes

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