Phenacyl bromide → HCID 57345350, compound

HRID 1619557Notes

Reaction equation

HRID 1619557 reaction equation
[C:1]1([CH:7]([NH:19][S:20]([CH2:23][C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)(=[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:30][CH2:31][C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)=[O:33]>CCOC(C)=O>[Br-:30].[O:33]=[C:32]([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[CH2:31][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:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)[NH:19][S:20]([CH2:23][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1)(=[O:22])=[O:21])[CH2:12]2

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 67605978HCID 67605978, compound

Product 1

HCID 57345350HCID 57345350, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-quinuclidin-3-yl 2-phenyl-2-(phenylmethylsulfonamido)-acetate (C80) (41 mg, 0.10 mmol) in EtOAc (2 ml), was added 2-bromo-1-phenylethanone (21.7 mg, 0.11 mmol), and the reaction was stirred at RT for 1 hour. The solvent was evaporated, and the crude was triturated with Et2O to obtain (3R)-1-(2-oxo-2-phenylethyl)-3-(2-phenyl-2-(phenylmethylsulfonamido)acetoxy)-1-azoniabicyclo[2.2.2]octane bromide (50 mg; 82% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe crude was triturated with Et2O

Sources & evidence

ORD record
ord-6ac7933f59ea4fb28ae9949a9a3a887b
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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