2-(Chloroacetyl)thiophene → (R)-3-{2-[(4-fluoro-phenyl)-methyl-amino]-2-phenyl-acetoxy}-1-(2-oxo-2-thiophen-2-yl-ethyl)-1-azonia-bicyclo[2.2.2]octane chloride

HRID 77040Notes

Reaction equation

HRID 77040 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:27])[CH:11]([N:18]([C:20]1[CH:25]=[CH:24][C:23]([F:26])=[CH:22][CH:21]=1)[CH3:19])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH2:2]2.[Cl:28][CH2:29][C:30]([C:32]1[S:33][CH:34]=[CH:35][CH:36]=1)=[O:31]>C(OCC)(=O)C>[Cl-:28].[F:26][C:23]1[CH:24]=[CH:25][C:20]([N:18]([CH3:19])[CH:11]([C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=2)[C:10]([O:9][C@@H:3]2[CH:4]3[CH2:7][CH2:8][N+:1]([CH2:29][C:30](=[O:31])[C:32]4[S:33][CH:34]=[CH:35][CH:36]=4)([CH2:6][CH2:5]3)[CH2:2]2)=[O:27])=[CH:21][CH:22]=1

Participants

4

Reactant 2

HCID 27579252-(Chloroacetyl)thiopheneHCID 58556953HCID 58556953, compound

Product 1

HCID 86643227(R)-3-{2-[(4-fluoro-phenyl)-methyl-amino]-2-phenyl-acetoxy}-1-(2-oxo-2-thiophen-2-yl-ethyl)-1-azonia-bicyclo[2.2.2]octane chlorideYield 84%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of [(4-fluoro-phenyl)-methyl-amino]-phenyl-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester (C120) (100 mg, 0.27 mmol) in ethyl acetate (2.7 mL), is added 2-chloro-1-(thiophen-2-yl)ethanone (48.0 mg, 0.30 mmol). The reaction is stirred at RT for 3.5 days. The suspension is evaporated and the residue is triturated with Et2O (8 mL). The solid is filtered on a buckner funnel and the sticky solid is dissolved in DCM. The solution is evaporated giving the title compound as a pale yellow solid (120 mg, 84% yield, chloride salt, mixture of diastereoisomers).

Workup

  1. customThe suspension is evaporated
  2. customthe residue is triturated with Et2O (8 mL)
  3. filtrationThe solid is filtered on a buckner funnel
  4. dissolutionthe sticky solid is dissolved in DCM
  5. customThe solution is evaporated

Sources & evidence

ORD record
ord-b6b6865559074f3cb208fd8268782bc3
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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