(R)-1-[2-(4-nitro-phenyl)-2-oxo-ethyl]-3-((R)-2-phenyl-2-phenylamino-acetoxy)-1-azonia-bicyclo[2.2.2]octane bromide → HCID 86643240, compound

HRID 77064Notes

Reaction equation

HRID 77064 reaction equation
[Br-].[N+:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:38])[CH2:12][N+:13]23[CH2:20][CH2:19][CH:16]([CH2:17][CH2:18]2)[C@@H:15]([O:21][C:22](=[O:37])[C@@H:23]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[NH:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH2:14]3)=[CH:7][CH:6]=1)([O-])=O>C1COCC1>[CH:22]([O-:37])=[O:21].[NH2:2][C:5]1[CH:10]=[CH:9][C:8]([C:11](=[O:38])[CH2:12][N+:13]23[CH2:18][CH2:17][CH:16]([CH2:19][CH2:20]2)[C@@H:15]([O:21][C:22](=[O:37])[C@@H:23]([C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=2)[NH:24][C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=2)[CH2:14]3)=[CH:7][CH:6]=1

Participants

3

Reactant 1

HCID 86643241(R)-1-[2-(4-nitro-phenyl)-2-oxo-ethyl]-3-((R)-2-phenyl-2-phenylamino-acetoxy)-1-azonia-bicyclo[2.2.2]octane bromide

Product 1

HCID 86643240HCID 86643240, compoundYield 79.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of (R)-1-[2-(4-nitro-phenyl)-2-oxo-ethyl]-3-((R)-2-phenyl-2-phenylamino-acetoxy)-1-azonia-bicyclo[2.2.2]octane bromide (Diastereoisomer 1 of C179) (88 mg, 0.152 mmol) in THF (30 mL) is hydrogenated in presence of a catalytic amount of Pt2O at 15 psi for 2 hours and then at 20 psi for additional 2 hours (UPLC-MS monitoring: complete conversion). Catalyst is removed by filtration and the solution evaporated to dryness. The crude is purified by preparative HPLC to give the title compound as a pale yellow solid (31 mg, 37% yield, formate formate anion, single diastereoisomer).

Workup

  1. customCatalyst is removed by filtration
  2. customthe solution evaporated to dryness
  3. customThe crude is purified by preparative HPLC

Sources & evidence

ORD record
ord-ece6702c0906455daf2bde29505265e2
Source dataset
uspto-grants-2014_09
Patent number
US08835682B2

Reaction notes

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