Ammonium Chloride → HCID 22875676, compound

HRID 2258013Notes

Reaction equation

HRID 2258013 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.[CH3:25][Mg]Br.[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]([CH3:25])([OH:10])[CH3:9])[CH2:6][CH2:5]1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 22875684HCID 22875684, compoundHCID 178418573HCID 178418573, compound

Product 1

HCID 22875676HCID 22875676, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 20 mg (0.06 mmol) 7β-methyl-5α-4-azapregn-1-ene-3,20-dione in 4 ml dry tetrahydrofuran at -40° C. under N2 was added 10 eq methylmagnesium bromide (0.6 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 16 mg (0.046 mmol, 77% 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-52661471781846f7b6f3b8a0d0f5e1ed
Source dataset
uspto-grants-1997_08
Patent number
US05658922

Reaction notes

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