Trifluoroacetic acid → (R)-1-Carboxymethyl-3-(2-hydroxy-2,2-diphenyl-acetoxy)-1-azonia-bicyclo[2.2.2]-octane trifluoroacetate

HRID 1920550Notes

Reaction equation

HRID 1920550 reaction equation
[Br-].C([O:6][C:7]([CH2:9][N+:10]12[CH2:17][CH2:16][CH:13]([CH2:14][CH2:15]1)[C@@H:12]([O:18][C:19](=[O:34])[C:20]([OH:33])([C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[CH2:11]2)=[O:8])(C)(C)C.[F:35][C:36]([F:41])([F:40])[C:37]([OH:39])=[O:38]>C(Cl)(Cl)Cl>[F:35][C:36]([F:41])([F:40])[C:37]([O-:39])=[O:38].[C:7]([CH2:9][N+:10]12[CH2:17][CH2:16][CH:13]([CH2:14][CH2:15]1)[C@@H:12]([O:18][C:19](=[O:34])[C:20]([OH:33])([C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1)[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1)[CH2:11]2)([OH:8])=[O:6]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 86611354(R)-1-tert-Butoxycarbonylmethyl-3-(2-hydroxy-2,2-diphenyl-acetoxy)-1-azonia-bicyclo[2.2.2]-octane bromide

Product 1

HCID 86611356(R)-1-Carboxymethyl-3-(2-hydroxy-2,2-diphenyl-acetoxy)-1-azonia-bicyclo[2.2.2]-octane trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of (R)-1-tert-Butoxycarbonylmethyl-3-(2-hydroxy-2,2-diphenyl-acetoxy)-1-azonia-bicyclo[2.2.2]octane bromide (Example 60) (0.14 g, 0.264 mmol) in chloroform (5 ml) is added trifluoroacetic acid (1 ml). The reaction mixture is left to stir at room temperature overnight. The solvent is removed in vacuo and purification of the residue by chromatography on C18 silica, eluting with water:acetonitrile affords the titled compound as a white solid.

Workup

  1. waitThe reaction mixture is left
  2. customThe solvent is removed in vacuo and purification of the residue by chromatography on C18 silica
  3. washeluting with water

Sources & evidence

ORD record
ord-08015c63889546c8a5c9ec6bfaa69c0f
Source dataset
uspto-grants-2012_05
Patent number
US08168654B2

Reaction notes

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