4-HYDROXY-2-METHOXY-BENZOIC ACID METHYL ESTER Chemical Properties

Melting point:

150-151℃

storage temp. 

Inert atmosphere,Room Temperature

Appearance

White to off-white Solid

Safety Information

HS Code 

2918999090

4-HYDROXY-2-METHOXY-BENZOIC ACID METHYL ESTER Usage And Synthesis

Uses

Methyl 4-?Hydroxy-?2-?methoxybenzoate is a reagent used in the synthesis of sphingosine-1-phosphate receptor agonist Ceralifimod used in the treatment of autoimmune diseases.

Synthesis

Step 3: A solution of EtOAc (200 mL) of methyl 2-methoxy-4-benzyloxybenzoate (40 g, 147 mmol) obtained in Step 2 was added to a Parr shaking flask, followed by 2 g of 10% Pd/C catalyst. The reaction mixture was placed in a Parr hydrogenation unit and shaken at 55 psi H2 pressure for 24 hours. Upon completion of the reaction, the catalyst was removed by filtration under argon protection and the solvent was removed by distillation under reduced pressure. The resulting solid was washed with a small amount of EtOAc, filtered and dried under vacuum for 24 h to give methyl 2-methoxy-4-hydroxybenzoate in 99% yield.

References

[1] Patent: US5665719, 1997, A
[2] Journal of Medicinal Chemistry, 1998, vol. 41, # 12, p. 2146 - 2163
[3] Bioorganic and Medicinal Chemistry Letters, 1998, vol. 8, # 21, p. 3081 - 3086
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 3, p. 1059 - 1062
[5] Journal of Medicinal Chemistry, 1985, vol. 28, # 6, p. 717 - 727

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