Ammonium Chloride → 1-benzyl-5-[4-(4-fluorophenyl)-1-hydroxy-1-(4-tert-butylaminocarbonylphenyl)butyl]-1-H-imidazole

HRID 744723Notes

Reaction equation

[C:1]([NH:5][C:6]([C:8]1[CH:13]=[CH:12][C:11](Br)=[CH:10][CH:9]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])CCC.[CH2:20]([N:27]1[C:31]([C:32](=[O:43])[CH2:33][CH2:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)=[CH:30][N:29]=[CH:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.[Cl-].[NH4+]>O1CCCC1.CCCCCC>[CH2:20]([N:27]1[C:31]([C:32]([OH:43])([C:11]2[CH:12]=[CH:13][C:8]([C:6]([NH:5][C:1]([CH3:4])([CH3:3])[CH3:2])=[O:7])=[CH:9][CH:10]=2)[CH2:33][CH2:34][CH2:35][C:36]2[CH:41]=[CH:40][C:39]([F:42])=[CH:38][CH:37]=2)=[CH:30][N:29]=[CH:28]1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

Conditions

Temperature: -70 °C

Procedure

9,9 g of p-tert-butylaminocarbonylphenyl bromide is dissolved in 200 ml of dry tetrahydrofuran and cooled to -70° C. To the solution is added dropwise n-butyl lithium (5,3 g) in hexane and the mixture is stirred for one hour. 1-benzyl-5-[4-(4-fluorophenyl)-1-oxobutyl]-1H-imidazole (10,4 g) in 200 ml of tetrahydrofuran is added to the mixture at -70° C. and the mixture is allowed to warm to room temperature and stirring is continued over night. Saturated ammonium chloride is added to the mixture and the solution is extracted with ethyl acetate. Ethyl acetate fractions are combined and evaporated to dryness.

Workup

temperatureto warm to room temperature
stirringstirring
waitis continued over night
extractionthe solution is extracted with ethyl acetate
customevaporated to dryness

Sources & evidence

ORD record: ord-3d543c7ead7d4e2db77bbcedf9e71a6c
Source dataset: uspto-grants-1996_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05559141

Reaction notes

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