Methanol → HCID 178499371, compound

HRID 896847Notes

Reaction equation

HRID 896847 reaction equation
[Br:1][CH:2]([CH2:6][C:7]1[N:8]=[CH:9][NH:10][CH:11]=1)[C:3]([OH:5])=[O:4].[CH3:12]O>>[Br:1][CH:2]([CH2:6][C:7]1[N:8]=[CH:9][NH:10][CH:11]=1)[C:3]([O:5][CH3:12])=[O:4]

Participants

3

Reactant 2

HCID 887MethanolHCID 178524988HCID 178524988, compound

Product 1

HCID 178499371HCID 178499371, compound

Procedure

Hydrogen chloride was bubbled through an ice-cooled solution of 2-bromo-3-(1H-imidazol-4-yl)propanoic acid (500 mg, 2.3 mmol) in methanol (15 ml) for 10 minutes, and the mixture was stirred at room temperature for 18 hours. The solution was evaporated under reduced pressure, the residue was suspended in ice-cooled sodium bicarbonate solution, and the suspension was extracted with dichloromethane (4×20 ml). The combined organic solutions were dried (Na2SO4) and evaporated under reduced pressure to afford the title compound as an oil, 600 mg. 1H-NMR (CDCl3, 300 MHz) δ: 3.24 (dd, 1H), 3.44 (dd, 1H), 3.78 (s, 3H), 4.58 (dd, 1H), 6.92 (s, 1H), 7.60 (s, 1H). LRMS: m/z (ES+) 233, 235 [MH+].

Workup

  1. customHydrogen chloride was bubbled through an ice-
  2. customThe solution was evaporated under reduced pressure
  3. temperaturecooled sodium bicarbonate solution
  4. extractionthe suspension was extracted with dichloromethane (4×20 ml)
  5. dry with materialThe combined organic solutions were dried (Na2SO4)
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c34ff06850294d14b9fc834baa863fea
Source dataset
uspto-grants-2005_07
Patent number
US06919457B2

Reaction notes

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