Trifluoroacetic acid → (R)-3-((S)-2-amino-phenylpropanoyloxy)-1-(2-phenoxyethyl)-1-azonia-bicyclo[2.2.2]octane trifluoroacetate trifluoroacetate

HRID 77031Notes

Reaction equation

HRID 77031 reaction equation
[Br-].C(OC([NH:9][C@@H:10]([CH2:31][C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:11]([O:13][C@@H:14]1[CH:19]2[CH2:20][CH2:21][N+:16]([CH2:22][CH2:23][O:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)([CH2:17][CH2:18]2)[CH2:15]1)=[O:12])=O)(C)(C)C.[F:38][C:39]([F:44])([F:43])[C:40]([OH:42])=[O:41]>C(Cl)Cl>[F:38][C:39]([F:44])([F:43])[C:40]([O-:42])=[O:41].[F:38][C:39]([F:44])([F:43])[C:40]([O-:42])=[O:41].[NH2:9][C@@H:10]([CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:11]([O:13][C@@H:14]1[CH:19]2[CH2:20][CH2:21][N+:16]([CH2:22][CH2:23][O:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)([CH2:17][CH2:18]2)[CH2:15]1)=[O:12].[NH2:9][C@@H:10]([CH2:31][C:32]1[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1)[C:11]([O:13][C@@H:14]1[CH:19]2[CH2:20][CH2:21][N+:16]([CH2:22][CH2:23][O:24][C:25]3[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=3)([CH2:17][CH2:18]2)[CH2:15]1)=[O:12]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 68468848HCID 68468848, compound

Product 1

HCID 86643220(R)-3-((S)-2-amino-phenylpropanoyloxy)-1-(2-phenoxyethyl)-1-azonia-bicyclo[2.2.2]octane trifluoroacetate trifluoroacetateYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (R)-3-((S)-2-tertbutoxycarbonylamino-phenylpropanoyloxy)-1-(2-phenoxyethyl)-1-azonia-bicyclo[2.2.2]octane bromide (I148) (0.53 mmol) in DCM (5 mL), is added trifluoroacetic acid (0.50 mL, 4.41 mmol) and the mixture stirred at RT overnight. The solvent is evaporated and the resulting crude is purified by preparative LC-MS in order to obtain the title compound as a brown gummy solid (112 mg, 43% overall yield, trifluoroacetate salt and trifluoroacetate anion, single diastereoisomer).

Workup

  1. customThe solvent is evaporated
  2. customthe resulting crude is purified by preparative LC-MS in order

Sources & evidence

ORD record
ord-92d71e6e05c24c478187cc0b30fb9e52
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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