Hydrogen Bromide → HCID 136206534, compound

HRID 1616614Notes

Reaction equation

HRID 1616614 reaction equation
C[O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][N:8]1[C:12]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19]C)=[CH:11][N:10]=[N:9]1.Br.[OH-].[Na+]>C(O)(=O)C>[OH:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:12]1[N:8]([CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:21])=[O:2])[N:9]=[N:10][CH:11]=1

Participants

5

Reactant 3

HCID 260Hydrogen Bromide2×HCID 14798Sodium HydroxideHCID 59167782HCID 59167782, compound

Product 1

HCID 136206534HCID 136206534, compoundYield 80.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Combine 5-[5-(2-methoxy-phenyl)-[1,2,3]triazol-1-yl]-pentanoic acid methyl ester (2.99 g, 10.3 mmol), hydrobromic acid (50 mL, 48% in water), and acetic acid (50 mL, glacial) and heat to reflux under N2 for 3 hours. Add hydrobromic acid (20 mL, 48% in water) and continue heating at reflux under N2 overnight. Cool to room temperature, basify to pH 4 with 5N NaOH solution. Extract from aqueous layer with EtOAc (×3), wash combined organic layers with brine, dry combined organic layers over MgSO4 and concentrate to get 2.6 yellow oil. Concentrate, adsorb on SiO2 and purify the residue by flash chromatography on silica gel eluting with 3-5% MeOH/CH2Cl2. Add Et2O and concentrate (×5) in order to remove solvents and afford the title compound (2.16 g, 80%). MS (IS) 262 (M+1)+.

Workup

  1. temperatureto reflux under N2 for 3 hours
  2. temperatureat reflux under N2 overnight
  3. extractionExtract from aqueous layer with EtOAc (×3)
  4. washwash
  5. dry with materialdry combined organic layers over MgSO4
  6. concentrationconcentrate
  7. customto get 2.6 yellow oil
  8. concentrationConcentrate
  9. custompurify the residue by flash chromatography on silica gel eluting with 3-5% MeOH/CH2Cl2
  10. concentrationAdd Et2O and concentrate (×5) in order
  11. customto remove solvents

Sources & evidence

ORD record
ord-cc306cab67c94dd49ce06272f5295ebc
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

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