Hydrochloric Acid → HCID 178470318, compound

HRID 869701Notes

Reaction equation

HRID 869701 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C@@H:12]([C:21]([NH:23][CH:24]([C:30](=O)[CH3:31])[C:25]([O:27][CH2:28][CH3:29])=[O:26])=[O:22])[NH:13]C(OC(C)(C)C)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl>C(O)C.O1CCOCC1>[CH2:1]([O:8][CH2:9][CH2:10][CH2:11][C:12]1[N:13]=[C:30]([CH3:31])[C:24]([C:25]([O:27][CH2:28][CH3:29])=[O:26])=[N:23][C:21]=1[OH:22])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 67395178ethyl 2-{[5-(benzyloxy)-N-(tert-butoxycarbonyl)-L-norvalyl]amino}-3-oxobutanoate

Product 1

HCID 178470318HCID 178470318, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
60 °C

Procedure

To a solution of ethyl 2-{[5-(benzyloxy)-N-(tert-butoxycarbonyl)-L-norvalyl]amino}-3-oxobutanoate (5.31 g, 11.8 mmol) in ethanol (20 mL) was added 4N hydrochloric acid in 1,4-dioxane (20 mL) at room temperature. After being stirred for 16 h at same temperature, the reaction mixture was concentrated in vacuo. A solution of the residue in pyridine (40 mL) was heated at 60° C. for 23 h. After being cooled to ambient temperature, the mixture was concentrated in vacuo. The residue was poured into water, and the mixture was extracted with chloroform. The organic layer was washed with water and saturated brine, dried over sodium sulfate, filtrated and concentrated in vacuo. To a solution of the residue in dichloromethane (20 mL) was added manganes dioxide (1.03 g) at room temperature. After being stirred for 1.5 h at same temperature, the reaction mixture was filtrated through celite with chloroform. The filtrate was combined and concentrated in vacuo. The crude was purified by silica gel column chromatography (chloroform to chloroform:methanol=19:1) to give ethyl 5-[3-(benzyloxy)propyl]-6-hydroxy-3-methylpyrazine-2-carboxylate. MS (APCI): m/z 331 (M+H).

Workup

  1. concentrationthe reaction mixture was concentrated in vacuo
  2. temperatureAfter being cooled to ambient temperature
  3. concentrationthe mixture was concentrated in vacuo
  4. additionThe residue was poured into water
  5. extractionthe mixture was extracted with chloroform
  6. washThe organic layer was washed with water and saturated brine
  7. dry with materialdried over sodium sulfate
  8. filtrationfiltrated
  9. concentrationconcentrated in vacuo
  10. additionTo a solution of the residue in dichloromethane (20 mL) was added manganes dioxide (1.03 g) at room temperature
  11. stirringAfter being stirred for 1.5 h at same temperature
  12. filtrationthe reaction mixture was filtrated through celite with chloroform
  13. concentrationconcentrated in vacuo
  14. customThe crude was purified by silica gel column chromatography (chloroform to chloroform:methanol=19:1)

Sources & evidence

ORD record
ord-c4bdc91c2035465890ace523e238fd6c
Source dataset
uspto-grants-2015_03
Patent number
US08969376B2

Reaction notes

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