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

HRID 15271ノート

反応式

HRID 15271 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒2 回HCID 962Water溶媒

反応条件

温度
23 °C

実験手順

(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.

後処理

  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

出典と根拠

ORDレコード
ord-7529db78da714541970b6db3c8435d32
出典データセット
uspto-grants-2010_06
特許番号
US07732449B2

反応ノート

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