HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

Phenacyl bromide → (R)-3-((R)-2-(benzyloxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide

HRID 1619515
Notes
Print preview

Reaction equation

HRID 1619515 reaction equation
[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:13]([O:15][C@@H:16]1[CH:21]2[CH2:22][CH2:23][N:18]([CH2:19][CH2:20]2)[CH2:17]1)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[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].[CH2:1]([O:8][C:9]([NH:11][C@H:12]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:13]([O:15][C@@H:16]1[CH:21]2[CH2:20][CH2:19][N+:18]([CH2:31][C:32](=[O:33])[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)([CH2:23][CH2:22]2)[CH2:17]1)=[O:14])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 6259Phenacyl bromideHCID 67605835(R)-((R)-quinuclidin-3-yl) 2-(benzyloxycarbonylamino)-2-phenylacetate

Product 1

HCID 86665826(R)-3-((R)-2-(benzyloxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromideYield 75.8%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of (R)—((R)-quinuclidin-3-yl) 2-(benzyloxy-carbonylamino)-2-phenylacetate (40 mg, 0.10 mmol) in EtOAc (3 ml), 2-bromo-1-phenylethanone (22.2 mg, 0.11 mmol) was added and the reaction was stirred at RT for 15 hours, and then the solvent was evaporated. The crude was purified by silica gel flash chromatography (DCM/MeOH=93/7) to obtain (R)-3-((R)-2-(benzyloxycarbonylamino)-2-phenylacetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane bromide (45.0 mg; 74.8% yield).

Workup

  1. customthe solvent was evaporated
  2. customThe crude was purified by silica gel flash chromatography (DCM/MeOH=93/7)

Sources & evidence

ORD record
ord-4f3fdbc39b464a26964d9ad4774d6428
Source dataset
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08772314B2

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes