Ammonium Chloride → HCID 18668560, compound

HRID 1059189Notes

Reaction equation

[C:1]([N:20]1[CH:24]=[C:23]([C:25]([C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([NH:39][C:40](=[O:42])[CH3:41])[CH:34]=3)=[CH:29][CH:28]=2)=[O:26])[N:22]=[CH:21]1)([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:43][Mg]Br.[Cl-].[NH4+]>C1COCC1>[OH:26][C:25]([C:27]1[CH:28]=[CH:29][C:30]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([NH:39][C:40](=[O:42])[CH3:41])[CH:34]=2)=[CH:31][CH:32]=1)([C:23]1[N:22]=[CH:21][N:20]([C:1]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[CH:24]=1)[CH3:43]

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of N-[4′-[(1-trityl-1H-imidazol-4-yl)carbonyl][1,1′-biphenyl]-3-yl]acetamide (800 mg) in THF (14 ml) was added dropwise a solution (1.0 M; 4.38 ml) of methylmagnesium bromide in THF at 0° C., and the mixture was stirred at 0° C. for 20 min. Saturated ammonium chloride was added to the reaction mixture and the mixture was extracted with ethyl acetate, washed with saturated brine and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure and the residue was recrystallized from ethyl acetate-methanol-hexane to give the title compound (823 mg) as colorless powder crystals.

Workup

extractionthe mixture was extracted with ethyl acetate
washwashed with saturated brine
dry with materialdried over anhydrous magnesium sulfate
customThe solvent was evaporated under reduced pressure
customthe residue was recrystallized from ethyl acetate-methanol-hexane

Sources & evidence

ORD record: ord-0f0e7d9d67e64961b16b0a6033c2ced1
Source dataset: uspto-grants-2003_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06518257B1

Reaction notes

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