Ammonium Acetate → HCID 178442423, compound

HRID 425409Notes

Reaction equation

C([O-])(=O)C.[NH4+:5].[CH3:6][C:7]([CH3:43])([CH2:41][CH3:42])[CH2:8][C:9](=O)[CH2:10][NH:11][C:12]([C:14]1([CH2:26][C:27]2[CH:32]=[CH:31][C:30]([C:33]3[CH:38]=[CH:37][C:36]([F:39])=[CH:35][N:34]=3)=[CH:29][CH:28]=2)[CH2:18][CH2:17][CH2:16][N:15]1[C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])=O>C(OCC)(=O)C.O>[CH3:6][C:7]([CH3:43])([CH2:41][CH3:42])[CH2:8][C:9]1[N:5]=[C:12]([C:14]2([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([C:33]4[CH:38]=[CH:37][C:36]([F:39])=[CH:35][N:34]=4)=[CH:29][CH:28]=3)[CH2:18][CH2:17][CH2:16][N:15]2[C:19]([O:21][C:22]([CH3:23])([CH3:24])[CH3:25])=[O:20])[NH:11][CH:10]=1

Participants

Conditions

Temperature: 160 °C

Procedure

Ammonium acetate (1.47 g, 19 mmol) was added to an ambient temperature solution of tert-butyl 2-{[(4,4-dimethyl-2-oxohexyl)amino]carbonyl}-2-[4-(5-fluoropyridin-2-yl)benzyl]pyrrolidine-1-carboxylate (200 mg, 0.38 mmol) in xylenes (10 mL). After stirring at 160° C. in a sealed tube overnight, the reaction mixture was diluted with ethyl acetate and water. The organic phase was dried (magnesium sulfate), filtered, and concentrated in vacuo. Chromatography over silica eluting with 0-100% ethyl acetate/hexane followed by high pressure liquid chromatography (KR100-5C18 100×21.2 mm column) eluting with 10-100% acetonitrile/water containing 0.05% trifluoroacetic acid afforded tert-butyl 2-[4-(2,2-dimethylbutyl)-1H-imidazol-2-yl]-2-[4-(5-fluoropyridin-2-yl)benzyl]pyrrolidine-1-carboxylate.

Workup

dry with materialThe organic phase was dried (magnesium sulfate)
filtrationfiltered
concentrationconcentrated in vacuo
washeluting with 10-100% acetonitrile/water containing 0.05% trifluoroacetic acid

Sources & evidence

ORD record: ord-8c8129d0237d49c08a503b483116080c
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106070B2

Reaction notes

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