Hydrogen Bromide → HCID 67497150, compound

HRID 1920548Notes

Reaction equation

HRID 1920548 reaction equation
[Br-:1].C(O[C:7]([NH:9][CH2:10][CH2:11][N+:12]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[C@@H:14]([O:20][C:21](=[O:36])[C:22]([OH:35])([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)[CH2:13]2)=[O:8])(C)(C)C.Br>O1CCOCC1>[Br-:1].[C:7]([NH:9][CH2:10][CH2:11][N+:12]12[CH2:19][CH2:18][CH:15]([CH2:16][CH2:17]1)[C@@H:14]([O:20][C:21](=[O:36])[C:22]([OH:35])([C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=1)[C:29]1[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=1)[CH2:13]2)(=[O:8])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 67497312HCID 67497312, compound

Product 1

HCID 67497150HCID 67497150, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a stirred suspension of (R)-1-(2-tert-butoxycarbonylamino-ethyl)-3-(2-hydroxy-2,2-diphenyl-acetoxy)-1-azonia-bicyclo[2.2.2]octane bromide (0.5 g, 1.04 mmol) in dioxane (25 ml) is added hydrogen bromide solution in dioxane (1 ml, prepared by bubbling HBr gas through dry, cooled dioxane). The reaction mixture is stirred at room temperature overnight. The solvent is removed in vacuo and purification of the crude residue by chromatography on C18 silica, eluting with water:acetonitrile affords the title compound as a brown solid.

Workup

  1. customThe solvent is removed in vacuo and purification of the crude residue by chromatography on C18 silica
  2. washeluting with water

Sources & evidence

ORD record
ord-2ffed611e95e4af785cd3901bb618765
Source dataset
uspto-grants-2012_05
Patent number
US08168654B2

Reaction notes

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