Réaction #43549

Équation de réaction

(R)-2-cyclohexylmethyl-N-[2-(4-fluoro-phenylamino)-ethyl]-succinamic acid methyl ester

Lithium hydroxide

→

(R)-2-cyclohexylmethyl-N-[2-(4-fluoro-phenylamino)-ethyl]-succinamic acid

Solvants

MeOH

H2O

methanol

Conditions de réaction

Traitement

1. 1
   Autreplaced in a 0° C.
2. 2
   Autrewas removed by evaporation
3. 3
   workup.ADDITIONEthyl acetate (75 mL) was added to the resulting solution
4. 4
   Extractionwas extracted with 1 M HCl (50 mL)
5. 5
   ExtractionThe aqueous phase was extracted 2×75 mL of ethyl acetate
6. 6
   Lavagethe combined organic phases were washed with saturated sodium bicarbonate (50 mL), saturated sodium chloride (50 mL)
7. 7
   Séchagedried over magnesium sulfate
8. 8
   Filtrationfiltered
9. 9
   Autreevaporated

Mode opératoire

(R)-2-cyclohexylmethyl-N-[2-(4-fluoro-phenylamino)-ethyl]-succinamic acid methyl ester (220 mg, 0.60 mmol, 1.0 eq.) was dissolved in a mixture of MeOH (4.5 mL) and H2O (3 mL) and placed in a 0° C. ice bath. Lithium hydroxide (30 mg, 1.25 mmol, 2.1 eq.) was added in one portion and allowed to stir for 8 hours, slowly warming to 23° C. After the reaction was judged complete by LC/MS, methanol was removed by evaporation. Ethyl acetate (75 mL) was added to the resulting solution and was extracted with 1 M HCl (50 mL). The aqueous phase was extracted 2×75 mL of ethyl acetate and the combined organic phases were washed with saturated sodium bicarbonate (50 mL), saturated sodium chloride (50 mL) dried over magnesium sulfate, filtered and evaporated to provide 183 mg of (R)-2-cyclohexylmethyl-N-[2-(4-fluoro-phenylamino)-ethyl]-succinamic acid an yellow oil (0.52 mmol, 86%) and was used directly in the following reaction.

Source