Phenacyl bromide → HCID 57345352, compound

HRID 1619555Notes

Reaction equation

HRID 1619555 reaction equation
[C:1]1([CH:7]([NH:19][S:20]([CH2:23][C:24]([F:27])([F:26])[F:25])(=[O:22])=[O:21])[C:8]([O:10][C@@H:11]2[CH:16]3[CH2:17][CH2:18][N:13]([CH2:14][CH2:15]3)[CH2:12]2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Br:28][CH2:29][C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)=[O:31]>CCOC(C)=O>[Br-:28].[O:31]=[C:30]([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH2:29][N+:13]12[CH2:18][CH2:17][CH:16]([CH2:15][CH2:14]1)[C@@H:11]([O:10][C:8](=[O:9])[CH:7]([C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[NH:19][S:20]([CH2:23][C:24]([F:26])([F:27])[F:25])(=[O:22])=[O:21])[CH2:12]2

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 67606490HCID 67606490, compound

Product 1

HCID 57345352HCID 57345352, compoundYield 6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-quinuclidin-3-yl 2-phenyl-2-(2,2,2-trifluoroethyl-sulfonamido)acetate (C78) (60 mg, 0.15 mmol) in EtOAc (2 ml), was added 2-bromo-1-phenylethanone (35.3 mg, 0.18 mmol). The reaction was stirred at RT for 16 hours. Then the solvent was evaporated, and the crude was purified by flash chromatography (DCM/MeOH=9/1) to obtain (3R)-1-(2-oxo-2-phenylethyl)-3-(2-phenyl-2-(2,2,2-trifluoroethylsulfonamido)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (5 mg; 6% yield).

Workup

  1. customThen the solvent was evaporated
  2. customthe crude was purified by flash chromatography (DCM/MeOH=9/1)

Sources & evidence

ORD record
ord-c11dfdd0e9724d8a81f69baa21e3a157
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

Loading…