Phenacyl bromide → HCID 57345136, compound

HRID 1619578Notes

Reaction equation

HRID 1619578 reaction equation
[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[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:29][CH2:30][C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:32]>C(#N)C>[Br-:29].[C:1]([O:5][C:6]([NH:8][C@@H:9]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([OH:28])=[CH:24][CH:23]=1)[C:10]([O:12][C@@H:13]1[CH:18]2[CH2:19][CH2:20][N+:15]([CH2:30][C:31](=[O:32])[C:33]3[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=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 67607403HCID 67607403, compound

Product 1

HCID 57345136HCID 57345136, compoundYield 19.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (S)—((R)-quinuclidin-3-yl) 2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)propanoate (260 mg, 0.67 mmol) in dry acetonitrile (10 ml), was added portionwise 2-bromo-1-phenylethanone (126 mg, 0.63 mmol). The reaction was stirred at RT for 3 hours. The solvent was evaporated, and the residue was purified by flash chromatography (DCM/MeOH=85/15), and the recovered product was triturated with i-PrOH to obtain (R)-3-((S)-2-(tert-butoxycarbonylamino)-3-(4-hydroxyphenyl)-propanoyloxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (74 mg, 18.8% yield).

Workup

  1. customThe solvent was evaporated
  2. customthe residue was purified by flash chromatography (DCM/MeOH=85/15)
  3. customthe recovered product was triturated with i-PrOH

Sources & evidence

ORD record
ord-c0b63aa6fce84f90b2734d481eb4f22b
Source dataset
uspto-grants-2014_07
Patent number
US08772314B2

Reaction notes

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