Hydrochloric Acid → HCID 68490692, compound

HRID 1616581Notes

Reaction equation

HRID 1616581 reaction equation
C[O:2][C:3](=[O:21])[CH2:4][CH2:5][CH2:6][CH2:7][C:8]1[O:9][C:10]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[O:19][CH3:20])=[CH:11][N:12]=1.[Li+].[OH-].Cl>O1CCOCC1.O>[CH3:20][O:19][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[C:10]1[O:9][C:8]([CH2:7][CH2:6][CH2:5][CH2:4][C:3]([OH:21])=[O:2])=[N:12][CH:11]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 591677925-[5-(2-Methoxy-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester

Product 1

HCID 68490692HCID 68490692, compoundYield 75.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

Dissolve 5-[5-(2-methoxy-phenyl)-oxazol-2-yl]-pentanoic acid methyl ester (2.47 g, 8.54 mmol) in 40 mL of dioxane and add a solution of LiOH (1.0344 g, 43.19 mmol) in 20 mL of water to the solution. Allow the reaction to stir at ambient temperature for 21 hours. Acidify the reaction with 5N HCl and concentrate the reaction mixture in vacuo to remove the dioxane. Extract the aqueous residue with EtOAc (3×). Dry the combined organic layers with MgSO4. Filter off the drying agent and concentrate in vacuo to afford a crude residue. Recrystallize the residue in EtOAc/hexanes to afford 1.7692 g of the titled product (75%): mass spectrum: m/z=276.1 (M+H).

Workup

  1. customthe reaction
  2. concentrationconcentrate the reaction mixture in vacuo
  3. customto remove the dioxane
  4. extractionExtract the aqueous residue with EtOAc (3×)
  5. dry with materialDry the combined organic layers with MgSO4
  6. filtrationFilter off the drying agent
  7. concentrationconcentrate in vacuo
  8. customto afford a crude residue
  9. customRecrystallize the residue in EtOAc/hexanes

Sources & evidence

ORD record
ord-fa4dc6c7db824d17a50532678682474a
Source dataset
uspto-grants-2014_07
Patent number
US08765796B2

Reaction notes

Loading…