Phenacyl bromide → HCID 57345134, compound

HRID 1619580Notes

Reaction equation

HRID 1619580 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH: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: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].[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:21][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:10]([O:12][C@@H:13]1[CH:18]2[CH2:19][CH2:20][N+:15]([CH2:29][C:30](=[O:31])[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)([CH2:16][CH2:17]2)[CH2:14]1)=[O:11])=[O:7])([CH3:4])([CH3:2])[CH3:3]

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 59401188(S)-((R)-quinuclidin-3-yl) 2-(tert-butoxycarbonylamino)-3-phenylpropanoate

Product 1

HCID 57345134HCID 57345134, compoundYield 84.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (S)—((R)-quinuclidin-3-yl) 2-(tert-butoxycarbonylamino)-3-phenylpropanoate (600 mg, 1.60 mmol) in EtOAc (10 ml), was added portionwise 2-bromo-1-phenylethanone (303 mg, 1.52 mmol). The reaction was stirred at RT for three days. The precipitate was collected by filtration and dried under vacuum to obtain (R)-3-((S)-2-(tert-butoxycarbonylamino)-3-phenylpropanoyloxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (740 mg, 81% yield).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. customdried under vacuum

Sources & evidence

ORD record
ord-955b3e85afaf4a7ab61a1ddd78952c40
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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