Hydrochloric Acid → HCID 28323176, compound

HRID 1779976Notes

Reaction equation

HRID 1779976 reaction equation
COC1[C@@H](C(C)C)N=[C:6]([O:17][CH3:18])[C@H:7]([CH2:9][C:10]2[C:11]([CH3:16])=[N:12][O:13][C:14]=2[CH3:15])[N:8]=1.Cl.[O:23]1CCOCC1>>[NH2:8][C@@H:7]([CH2:9][C:10]1[C:11]([CH3:16])=[N:12][O:13][C:14]=1[CH3:15])[C:6]([O:17][CH3:18])=[O:23]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 312751,4-DioxaneHCID 57149884HCID 57149884, compound

Product 1

HCID 28323176HCID 28323176, compound

Procedure

A mixture of (2R,5S)-2,5-dihydro-3,6-dimethoxy-2-isopropyl-5-(3,5-dimethyl-4-isoxazolylmethyl)pyrazine (2 g, 6.8 mmol), 1.0M HCl (13.6 ml, 13.6 mmol) and dioxane (13.6 ml) was stirred at ambient temperature overnight under N2. Dioxane was removed under reduced pressure and the water phase extracted with diethyl ether (20 ml). Aqueous ammonia was added to the water phase until pH 9, extracted with CHCl3 (3×30 ml), dried (MgSO4) and the solvent removed under reduced pressure. The valine methyl ester was removed by bulb-to-bulb distillation at 40°-50° C. (0.05 mbar). The undistilled title compound was used without further purification.

Workup

  1. customDioxane was removed under reduced pressure
  2. extractionthe water phase extracted with diethyl ether (20 ml)
  3. additionAqueous ammonia was added to the water phase until pH 9
  4. extractionextracted with CHCl3 (3×30 ml)
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed under reduced pressure
  7. customThe valine methyl ester was removed by bulb-to-bulb distillation at 40°-50° C. (0.05 mbar)
  8. distillationThe undistilled title compound was used without further purification

Sources & evidence

ORD record
ord-e81cb15a2e9a4f81b7a721736a5df376
Source dataset
uspto-grants-1997_05
Patent number
US05629293

Reaction notes

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