Phenacyl bromide → HCID 86665850, compound

HRID 1619549Notes

Reaction equation

HRID 1619549 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH:11][CH:12]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:13]([O:15][C@@H:16]2[CH:21]3[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]3)[CH2:17]2)=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=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].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([NH:11][CH:12]([C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:13]([O:15][C@@H:16]2[CH:21]3[CH2:20][CH2:19][N+:18]([CH2:31][C:32](=[O:33])[C:34]4[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=4)([CH2:23][CH2:22]3)[CH2:17]2)=[O:14])(=[O:10])=[O:9])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 67607872HCID 67607872, compound

Product 1

HCID 86665850HCID 86665850, compoundYield 42.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-quinuclidin-3-yl 2-(4-chlorophenylsulfonamido)-2-phenylacetate (C70) (62 mg, 0.14 mmol) in EtOAc (2.5 ml), was added 2-bromo-1-phenylethanone (31.2 mg, 0.16 mmol), and the reaction was stirred at RT for 3 hours. Then the solvent was evaporated, and the crude was triturated with Et2O to obtain (3R)-3-(2-(4-chlorophenylsulfonamido)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (38 mg; 42% yield).

Workup

  1. customThen the solvent was evaporated
  2. customthe crude was triturated with Et2O

Sources & evidence

ORD record
ord-93a0e93cd7df4ef987a9d88b02cd89b1
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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