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

HRID 1783859Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1783859
C[O:2][C:3](=[O:26])[C@H:4]([CH2:19][CH:20]1[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1)[CH2:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=1)=[O:7].[OH-].[Li+]>CO.O>[CH:20]1([CH2:19][C@H:4]([CH2:5][C:6]([NH:8][CH2:9][CH2:10][NH:11][C:12]2[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=2)=[O:7])[C:3]([OH:26])=[O:2])[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1

Komponenten

5

Edukt 2

HCID 3939Lithium HydroxideHCID 68481422(R)-2-cyclohexylmethyl-N-[2-(4-fluoro-phenylamino)-ethyl]-succinamic acid methyl ester

Produkt 1

HCID 68477765(R)-2-cyclohexylmethyl-N-[2-(4-fluoro-phenylamino)-ethyl]-succinamic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittel2×HCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

(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.

Aufarbeitung

  1. customplaced in a 0° C.
  2. customwas removed by evaporation
  3. additionEthyl acetate (75 mL) was added to the resulting solution
  4. extractionwas extracted with 1 M HCl (50 mL)
  5. extractionThe aqueous phase was extracted 2×75 mL of ethyl acetate
  6. washthe combined organic phases were washed with saturated sodium bicarbonate (50 mL), saturated sodium chloride (50 mL)
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. customevaporated

Quellen und Nachweise

ORD-Eintrag
ord-d0407a9318944a7e917dcccb34ff3fef
Quelldatensatz
uspto-grants-2009_03
Patentnummer
US07501408B2

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