Phenacyl bromide → HCID 86665858, compound

HRID 1619574Notes

Reaction equation

HRID 1619574 reaction equation
[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1)[C:10]([O:12][C@@H:13]1[CH:18]2[CH2:19][CH2:20][N:15]([CH2:16][CH2:17]2)[CH2:14]1)=[O:11])=[O:7])([CH3:4])([CH3:3])[CH3:2].[Br:31][CH2:32][C:33]([C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)=[O:34]>CCOC(C)=O>[Br-:31].[C:1]([O:5][C:6]([NH:8][CH:9]([CH2:21][C:22]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[NH:24][CH:23]=1)[C:10]([O:12][C@@H:13]1[CH:18]2[CH2:17][CH2:16][N+:15]([CH2:32][C:33](=[O:34])[C:35]3[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=3)([CH2:20][CH2:19]2)[CH2:14]1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 67605892HCID 67605892, compound

Product 1

HCID 86665858HCID 86665858, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)-quinuclidin-3-yl 2-(tert-butoxycarbonylamino)-3-(1H-indol-3-yl)propanoate (95 mg, 0.23 mmol) in EtOAc (3 ml), was added 2-bromo-1-phenylethanone (54.9 mg, 0.28 mmol), and the reaction was stirred at RT for 15 hours. The solid was collected by filtration and purified by silica gel flash chromatography (DCM/MeOH=94/6) to obtain (3R)-3-(2-(tert-butoxycarbonylamino)-3-(1H-indol-3-yl)propanoyloxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (31.0 mg, 22% yield).

Workup

  1. filtrationThe solid was collected by filtration
  2. custompurified by silica gel flash chromatography (DCM/MeOH=94/6)

Sources & evidence

ORD record
ord-38202db72b894c3481985b6387518045
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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