Hydrochloric Acid → HCID 178525395, compound

HRID 870574Notes

Reaction equation

HRID 870574 reaction equation
CO.[N:3]1[N:4]=[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([O:14]C)=[O:13])[NH:6][CH:7]=1.[OH-].[Li+].Cl>O.O1CCCC1>[N:3]1[N:4]=[C:5]([CH2:8][CH2:9][CH2:10][CH2:11][C:12]([OH:14])=[O:13])[NH:6][CH:7]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 3939Lithium HydroxideHCID 178500187HCID 178500187, compound

Product 1

HCID 178525395HCID 178525395, compoundYield 346.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Add methanol (3 mL), tetrahydrofuran (3 mL), and water (2 mL) to a flask containing methyl 5-(4H-1,2,4-triazol-3-yl)pentanoate (0.5 g; 1.0 equiv; 2.73 mmoles). Add lithium hydroxide (0.261 g; 4.0 equiv; 10.92 mmoles) in one portion, and stir at room temperature for 90 minutes. Cool the solution to 0° C. and add 5N hydrogen chloride (2.18 mL; 4.0 equiv; 10.92 mmoles) slowly. Concentrate the mixture and then azeotrope the residue with toluene (4×10 mL). Add dichloromethane (30 mL) followed by magnesium sulfate. Filter, and rinse the filter cake with 100 mL 10% ethanol in dichloromethane. Concentrate to provide 5-(4H-1,2,4-triazol-3-yl)pentanoic acid (1.6 g; >100%) as an alcoholic adduct: MS (m/z): 170 (M+1).

Workup

  1. concentrationConcentrate the mixture
  2. filtrationFilter
  3. washrinse the filter cake with 100 mL 10% ethanol in dichloromethane
  4. concentrationConcentrate

Sources & evidence

ORD record
ord-02da9a5f37fc428a9c896360c8fd64ce
Source dataset
uspto-grants-2015_03
Patent number
US08969555B2

Reaction notes

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