2-Chloroacetophenone → HCID 86660326, compound

HRID 469468Notes

Reaction equation

HRID 469468 reaction equation
[S:1]1[CH:5]=[C:4]([C@H:6]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:7]([O:9][C@@H:10]2[CH:15]3[CH2:16][CH2:17][N:12]([CH2:13][CH2:14]3)[CH2:11]2)=[O:8])[C:3]2[CH:25]=[CH:26][CH:27]=[CH:28][C:2]1=2.[Cl:29][CH2:30][C:31]([C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:32]>CC#N>[Cl-:29].[S:1]1[CH:5]=[C:4]([C@H:6]([NH:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:7]([O:9][C@@H:10]2[CH:15]3[CH2:16][CH2:17][N+:12]([CH2:30][C:31](=[O:32])[C:33]4[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=4)([CH2:13][CH2:14]3)[CH2:11]2)=[O:8])[C:3]2[CH:25]=[CH:26][CH:27]=[CH:28][C:2]1=2

Participants

4

Reactant 2

HCID 107572-ChloroacetophenoneHCID 58556996HCID 58556996, compound

Product 1

HCID 86660326HCID 86660326, compoundYield 31.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of (S)—((R)-quinuclidin-3-yl) 2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetate (diastereomer 2 of C19) (230 mg, 0.586 mmol) and 2-chloro-1-phenylethanone (91 mg, 0.586 mmol) in dry CH3CN (2 ml) was stirred at r.t. for 24 hours. Then the solvent was evaporated and the residue was purified by preparative HPLC (Eluent: CH3CN/H2O) to obtain (R)-3-((S)-2-(benzo[b]thiophen-3-yl)-2-(phenylamino)acetoxy)-1-(2-oxo-2-phenylethyl)-1-azoniabicyclo[2.2.2]octane chloride (102 mg, 31.8% yield).

Workup

  1. customThen the solvent was evaporated
  2. customthe residue was purified by preparative HPLC (Eluent: CH3CN/H2O)

Sources & evidence

ORD record
ord-de7c7d60393c4e399da208ef5527436c
Source dataset
uspto-grants-2014_01
Patent number
US08629160B2

Reaction notes

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