Phenacyl bromide → (R)-1-(2-oxo-2-phenyl-ethyl)-3-(2-phenyl-4-methyl-phenyl-amino-acetoxy)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 77049

Reaction equation

[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:26])[C:11]([C:19]1[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=1)([NH2:18])C1C=CC=CC=1)[CH2:2]2.[Br:27][CH2:28][C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)=[O:30]>C(#N)C>[Br-:27].[O:30]=[C:29]([C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)[CH2:28][N+:1]12[CH2:6][CH2:5][CH:4]([CH2:7][CH2:8]1)[C@@H:3]([O:9][C:10](=[O:26])[CH:11]([C:19]1[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][C:24]=1[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)[NH2:18])[CH2:2]2

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 4-methyl-phenyl-amino-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (C245) (63.5 mg, 0.18 mmol) in acetonitrile (5 mL), is added 2-bromo-1-phenyl-ethanone (36 mg, 0.18 mmol) and the mixture was heated at 100° C. for 1 hour in a MW oven (UPLC-MS monitoring: complete conversion). Solvent is evaporated and the resulting crude is purified by flash chromatography (DCM/MeOH=95/5) to obtain the title compound as a white solid (58 mg, 32% yield, bromide salt, mixture of diastereoisomers).

Workup

customSolvent is evaporated
customthe resulting crude is purified by flash chromatography (DCM/MeOH=95/5)

Sources & evidence

ORD record: ord-510ecd61bbac4a6dbd35ee21b4f498cd
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835682B2

Linked notes

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