Hydrochloric Acid → HCID 57991933, compound

HRID 2075370Notes

Reaction equation

HRID 2075370 reaction equation
C([C@@H]1C(OC)=[N:8][C@@H:7]([C@@H:12]([O:23][CH3:24])[C:13]2[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=2)[C:6]([O:25][CH3:26])=N1)(C)C.Cl.C1C[O:31]CC1>CC#N>[NH2:8][C@@H:7]([C@@H:12]([O:23][CH3:24])[C:13]1[CH:18]=[CH:17][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:15][CH:14]=1)[C:6]([O:25][CH3:26])=[O:31]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 57991935HCID 57991935, compound

Product 1

HCID 57991933HCID 57991933, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (2R,5S)-2-isopropyl-3,6-dimethoxy-5-((S)-methoxy(4-(trifluoromethyl)phenyl)methyl)-2,5-dihydropyrazine (3.40 g, 9.1 mmol) in THF (25 mL) and CH3CN (50 mL) was added 0.25 N hydrochloric acid (73 mL, 18 mmol) at room temperature. The mixture was stirred overnight and the solvent was removed in vacuo. The residue was neutralized with saturated NaHCO3 and extracted with ether. The organic layer was dried over Na2SO4 and concentrated in vacuo. The resulting residue was purified by silica gel chromatography (30%-50% EtOAc-hexane) to provide the product as a colorless oil (1.1 g, 43%). LCMS (API-ES) m/z (%): 278 (M+H).

Workup

  1. customthe solvent was removed in vacuo
  2. extractionextracted with ether
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe resulting residue was purified by silica gel chromatography (30%-50% EtOAc-hexane)

Sources & evidence

ORD record
ord-040031cceee048cc95f025beb87db3b3
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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