Hydrochloric Acid → HCID 86687870, compound

HRID 538096Notes

Reaction equation

HRID 538096 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([CH2:7][C:8]2[CH:9]=[C:10]([CH2:14][C:15]([O:17]C(C)(C)C)=[O:16])[CH:11]=[CH:12][CH:13]=2)[O:4][N:3]=1.Cl>O1CCOCC1>[CH3:1][C:2]1[N:6]=[C:5]([CH2:7][C:8]2[CH:9]=[C:10]([CH2:14][C:15]([OH:17])=[O:16])[CH:11]=[CH:12][CH:13]=2)[O:4][N:3]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 86687869HCID 86687869, compound

Product 1

HCID 86687870HCID 86687870, compoundYield 40.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

To a mixture of tert-butyl 2-(3-((3-methyl-1,2,4-oxadiazol-5-yl)methyl)phenyl)acetate 1099 (0.127 g, 0.44 mmol) in dioxane (3 mL) was added 4N HCl in dioxane (1 mL) and stirred under an atmosphere of argon for 2 hours. The volatiles were removed under reduced pressure and the residue diluted with water (5 mL) and the pH adjusted to 12 with 2.5 N NaOH. The mixture was washed with dichloromethane (4×2 mL) and the pH adjusted to 6 with 1 N HCl. The mixture was extracted with EtOAc (3×2 mL) and the organic layers combined, washed with brine and dried over Na2SO4. The Na2SO4 was removed by filtration and the volatiles removed under reduced pressure to give 0.041 g of 2-(3-((3-methyl-1,2,4-oxadiazol-5-yl)methyl)phenyl)acetic acid 1100. 1H NMR 300 MHz CDCl3: δ 7.40-7.18 (m, 4H), 4.18 (s, 2H), 3.63 (s, 2H), 2.36 (s, 3H).

Workup

  1. customThe volatiles were removed under reduced pressure
  2. additionthe residue diluted with water (5 mL)
  3. washThe mixture was washed with dichloromethane (4×2 mL)
  4. extractionThe mixture was extracted with EtOAc (3×2 mL)
  5. washwashed with brine
  6. dry with materialdried over Na2SO4
  7. customThe Na2SO4 was removed by filtration
  8. customthe volatiles removed under reduced pressure

Sources & evidence

ORD record
ord-6a76c7df7ca94433a256e05c45bd5305
Source dataset
uspto-grants-2014_10
Patent number
US08865718B2

Reaction notes

Loading…