Methanol → HCID 86753385, compound

HRID 1455961Notes

Reaction equation

HRID 1455961 reaction equation
[CH2:1]([O:8][C:9]1[C:14]([CH:15]([NH:18][C:19]2[CH:29]=[CH:28][C:22](C(OCC)=O)=[CH:21][CH:20]=2)[CH2:16][CH3:17])=[N:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:30][OH:31].[OH-:32].[Na+]>C1COCC1>[CH2:1]([O:8][C:9]1[C:14]([CH:15]([NH:18][C:19]2[CH:29]=[CH:28][CH:22]=[CH:21][C:20]=2[C:30]([OH:32])=[O:31])[CH2:16][CH3:17])=[N:13][CH:12]=[CH:11][N:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 22105517HCID 22105517, compound

Product 1

HCID 86753385HCID 86753385, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 4-(1-(2-benzyloxypyrazin-3-yl)prop-1-ylamino)benzoate (229 mg) was dissolved in THF (7 mL) and methanol (7 mL) and sodium hydroxide solution added (1.5 mL, 2M). The mixture was stirred for seventeen hours at ambient temperature, then heated at reflux for 2 hours, allowed to cool to ambient temperature and then the solvents evaporated off. The resulting foam was dissolved in water (25 mL) and extracted with ethyl acetate (2×20 mL) the aqueous phase was then adjusted to pH 4-5 with glacial acetic acid and re-extracted with ethyl acetate (2×20 mL). The combined organic phases were dried over magnesium sulphate. After removal of solvents, the residue was purified by MPLC (1% acetic acid, 24% ethyl acetate in hexane, silica)to give a yellow gum which was further purified by crystallisation from the above eluent system to give 4-(1-(2-benzyloxypyrazin-3-yl)prop-1-ylamino benzoic acid (138 mg, mp 141.5° C.).

Workup

  1. temperatureheated
  2. temperatureat reflux for 2 hours
  3. temperatureto cool to ambient temperature
  4. customthe solvents evaporated off
  5. dissolutionThe resulting foam was dissolved in water (25 mL)
  6. extractionextracted with ethyl acetate (2×20 mL) the aqueous phase
  7. extractionre-extracted with ethyl acetate (2×20 mL)
  8. dry with materialThe combined organic phases were dried over magnesium sulphate
  9. customAfter removal of solvents
  10. customthe residue was purified by MPLC (1% acetic acid, 24% ethyl acetate in hexane, silica)
  11. customto give a yellow gum which
  12. customwas further purified by crystallisation from the above eluent system

Sources & evidence

ORD record
ord-83894c06ee1b4c98bc454212ccac4bd9
Source dataset
uspto-grants-1998_12
Patent number
US05843942

Reaction notes

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