Potassium Carbonate → (3-{4-[(2-Chloro-3-(trifluoromethyl)benzyl)-(2,2-diphenylethyl)-amino]butyl}phenyl)-acetic Acid

HRID 902624Notes

Reaction equation

C[O:2][C:3](=[O:26])[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH2:12][CH2:13][CH2:14]OS(C2C=CC(C)=CC=2)(=O)=O)[CH:6]=1.[C:27]1([CH:33]([C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)[CH2:34][NH:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[C:39]([C:43]([F:46])([F:45])[F:44])[C:38]=2[Cl:47])[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C.O>[Cl:47][C:38]1[C:39]([C:43]([F:44])([F:45])[F:46])=[CH:40][CH:41]=[CH:42][C:37]=1[CH2:36][N:35]([CH2:34][CH:33]([C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[CH2:14][CH2:13][CH2:12][CH2:11][C:7]1[CH:6]=[C:5]([CH2:4][C:3]([OH:2])=[O:26])[CH:10]=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of {3-[4-(toluene-4-sulfonyloxy)butyl]phenyl}acetic acid methyl ester, (2,2-diphenylethyl)-(2-chloro-3-trifluoromethylbenzyl)amine (73 mg, 0.19 mmol), and potassium carbonate (26 mg, 0.21 mmol) in acetonitrile (5 ml) was stirred and heated to 50° C. for 5 hr. The reaction was cooled, diluted with water, and extracted with diethyl ether. The organic extracts were washed with water, dried, and the solvent removed. The residue was chromatographed over silica gel (hexane/methylene chloride/Diethyl ether:60/40/5) to give the title compound as an oil (35 mg, 31%). MS (ESI) 594.2 (M+H)+.

Workup

temperatureThe reaction was cooled
extractionextracted with diethyl ether
washThe organic extracts were washed with water
customdried
customthe solvent removed
customThe residue was chromatographed over silica gel (hexane/methylene chloride/Diethyl ether:60/40/5)

Sources & evidence

ORD record: ord-8c28f4db07e44bd0b627e2cb32184108
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365085B2

Reaction notes

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