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

HRID 15271노트

반응식

HRID 15271 반응식
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

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매2회HCID 962Water용매

반응 조건

온도
23 °C

실험 절차

(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.

후처리

  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

출처 및 근거

ORD 기록
ord-7529db78da714541970b6db3c8435d32
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732449B2

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