Hydrochloric Acid → HCID 58488311, compound

HRID 2075414Notes

Reaction equation

HRID 2075414 reaction equation
[Si:1]([O:8][C@@H:9]([C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=1)[C@H:10]1[C:15]([O:16]C)=N[C@H](C(C)C)C(OC)=[N:11]1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].Cl.C1C[O:37][CH2:36]C1>CC#N>[NH2:11][C@@H:10]([C@@H:9]([O:8][Si:1]([C:4]([CH3:7])([CH3:5])[CH3:6])([CH3:2])[CH3:3])[C:23]1[CH:28]=[CH:27][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:25][CH:24]=1)[C:15]([O:37][CH3:36])=[O:16]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 58488250HCID 58488250, compound

Product 1

HCID 58488311HCID 58488311, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of (2S,5R)-2-((S)-(tert-butyldimethylsilyloxy)(4-(trifluoromethyl)phenyl)methyl)-5-isopropyl-3,6-dimethoxy-2,5-dihydropyrazine (3.1 g, 6.6 mmol) in THF (15 mL) and CH3CN (30 mL) was added 0.25 N hydrochloric acid (53 mL, 13 mmol) at room temperature. The mixture was stirred over the weekend and then concentrated in vacuo. The residue was neutralized with saturated NaHCO3 and extracted with EtOAc three times. The organic layer was dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography on silica gel (0-25%-50% EtOAc-hexane) to provide the product as colorless oil (2.1 g, 84%). LCMS (API-ES) m/z: 378 (M+H+).

Workup

  1. concentrationconcentrated in vacuo
  2. extractionextracted with EtOAc three times
  3. dry with materialThe organic layer was dried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography on silica gel (0-25%-50% EtOAc-hexane)

Sources & evidence

ORD record
ord-195fa8605242447c8663f3a4f0fa3aa9
Source dataset
uspto-grants-2011_04
Patent number
US07919504B2

Reaction notes

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