Sodium Methoxide → HCID 57699112, compound

HRID 910787Notes

Reaction equation

HRID 910787 reaction equation
C[O-].[Na+].FC(F)(F)[C:6]([OH:8])=O.[CH2:11]([N:13]1[C:17](S(C)(=O)=O)=[N:16][N:15]=[C:14]1[C@H:22]([NH2:24])[CH3:23])[CH3:12]>CCOCC>[CH2:11]([N:13]1[C:17]([O:8][CH3:6])=[N:16][N:15]=[C:14]1[C@H:22]([NH2:24])[CH3:23])[CH3:12]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 67387632HCID 67387632, compound

Product 1

HCID 57699112HCID 57699112, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

NaOMe (18 ml, 2.0N, MeOH solution) was added to the (R)-1-(4-ethyl-5-methanesulfonyl-4H-[1,2,4]triazol-3-yl)ethylamine trifluoroacetate (3.0 g) obtained in Example 8-(6), and the mixture was heated for 1 hour under reflux. The reaction mixture was cooled to room temperature, and Et2O (100 ml) was added. After the mixture was cooled to 0° C., precipitated crystals were filtered. The filtrate was concentrated, and the resulting crude product was purified by NH silica gel chromatography using a solvent mixture of Et2O and MeOH to obtain the captioned compound (Compound 519) as a colorless oily substance (1.55 g).

Workup

  1. temperaturethe mixture was heated for 1 hour
  2. temperatureunder reflux
  3. temperatureAfter the mixture was cooled to 0° C.
  4. customprecipitated crystals
  5. filtrationwere filtered
  6. concentrationThe filtrate was concentrated
  7. customthe resulting crude product was purified by NH silica gel chromatography
  8. additiona solvent mixture of Et2O and MeOH

Sources & evidence

ORD record
ord-9fdd5d546c654cf4ae18ba661d57fdee
Source dataset
uspto-grants-2011_09
Patent number
US08022225B2

Reaction notes

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