Ammonium Chloride → HCID 59389313, compound

HRID 2357945Notes

Reaction equation

HRID 2357945 reaction equation
[CH2:1]([Mg]Br)[CH3:2].O1CCCC1.[CH3:10][O:11][CH2:12][C:13]1[N:18]2[N:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=[C:17]2[C:16]([CH:26]=[O:27])=[CH:15][CH:14]=1.[Cl-].[NH4+]>O1CCCC1>[OH:27][CH:26]([C:16]1[C:17]2[N:18]([N:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[CH:21]=2)[C:13]([CH2:12][O:11][CH3:10])=[CH:14][CH:15]=1)[CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 59389321HCID 59389321, compoundHCID 178420660HCID 178420660, compound

Product 1

HCID 59389313HCID 59389313, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In an argon atmosphere, a 0.97 mol/L ethyl magnesium bromide-tetrahydrofuran solution (12.0 mL) was added dropwise to a solution of the compound of Example 327 (2.00 g) in tetrahydrofuran (50 mL) at −78° C. The mixture was allowed to gradually warm to room temperature. A saturated aqueous ammonium chloride solution was added and the mixture was extracted with ethyl acetate (200 mL). The organic layer was washed sequentially with water and saturated brine and dried over anhydrous sodium sulfate. The extract was concentrated and purified by silica gel column chromatography (hexane:ethyl acetate=7:1→2:1) to afford the title compound as a colorless powder (1.68 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (200 mL)
  2. washThe organic layer was washed sequentially with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationThe extract was concentrated
  5. custompurified by silica gel column chromatography (hexane:ethyl acetate=7:1→2:1)

Sources & evidence

ORD record
ord-965a036057cd4284bc3c1343c16de6e0
Source dataset
uspto-grants-2010_07
Patent number
US07763617B2

Reaction notes

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