2-bromo-N-(isoxazol-3-yl)acetamide → (R)-3-[2-Hydroxy-2,2-bis-(3-methoxy-phenyl)-acetoxy]-1-(isoxazol-3-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide

HRID 2240318Notes

Reaction equation

HRID 2240318 reaction equation
[N:1]12[CH2:8][CH2:7][CH:4]([CH2:5][CH2:6]1)[C@@H:3]([O:9][C:10](=[O:29])[C:11]([OH:28])([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[CH2:2]2.[Br:30][CH2:31][C:32]([NH:34][C:35]1[CH:39]=[CH:38][O:37][N:36]=1)=[O:33]>C(#N)C>[Br-:30].[OH:28][C:11]([C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([O:26][CH3:27])[CH:21]=1)([C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([O:18][CH3:19])[CH:13]=1)[C:10]([O:9][C@@H:3]1[CH:4]2[CH2:7][CH2:8][N+:1]([CH2:31][C:32](=[O:33])[NH:34][C:35]3[CH:39]=[CH:38][O:37][N:36]=3)([CH2:6][CH2:5]2)[CH2:2]1)=[O:29]

Participants

4

Reactant 2

HCID 133629192-bromo-N-(isoxazol-3-yl)acetamideHCID 86627867Hydroxy-bis-(3-methoxy-phenyl)-acetic acid (R)-(1-aza-bicyclo[2.2.2]oct-3-yl)ester2×

Product 1

HCID 11628629(R)-3-[2-Hydroxy-2,2-bis-(3-methoxy-phenyl)-acetoxy]-1-(isoxazol-3-ylcarbamoylmethyl)-1-azonia-bicyclo[2.2.2]octane bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred solution of hydroxy-bis-(3-methoxy-phenyl)-acetic acid (R)-(1-aza-bicyclo[2.2.2]-oct-3-yl) ester (Intermediate K) (0.25 g, 0.63 mmol) in acetonitrile (10 ml) is added 2-bromo-N-isoxazol-3-yl-acetamide (0.15 g, 0.73 mmol) and the reaction mixture stirred at room temperature for 3 hours. The resulting precipitate is removed by filtration and the mother liquor is left at room temperature for 72 hours to crystallise. The crystals are filtered and dried in vacuo to yield the titled compound as a solid.

Workup

  1. customThe resulting precipitate is removed by filtration
  2. waitthe mother liquor is left at room temperature for 72 hours
  3. customto crystallise
  4. filtrationThe crystals are filtered
  5. customdried in vacuo

Sources & evidence

ORD record
ord-3967cfcc46dc4ad3ba96f0c466c8bef7
Source dataset
uspto-grants-2010_05
Patent number
US07723356B2

Reaction notes

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