Hydrochloric Acid → cis(+/-)-2-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-fluoropiperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylic acid

HRID 43837ノート

反応式

HRID 43837 の反応式
[OH-].[Li+].[Cl:3][C:4]1[N:5]=[C:6]([C:11]([NH:13][C@H:14]2[CH2:19][CH2:18][N:17]([C:20]3[S:21][C:22]([C:26]([O:28]CC)=[O:27])=[C:23]([CH3:25])[N:24]=3)[CH2:16][C@H:15]2[F:31])=[O:12])[NH:7][C:8]=1[CH2:9][CH3:10].Cl.O>CO.O1CCCC1>[Cl:3][C:4]1[N:5]=[C:6]([C:11]([NH:13][C@H:14]2[CH2:19][CH2:18][N:17]([C:20]3[S:21][C:22]([C:26]([OH:28])=[O:27])=[C:23]([CH3:25])[N:24]=3)[CH2:16][C@H:15]2[F:31])=[O:12])[NH:7][C:8]=1[CH2:9][CH3:10]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3939Lithium HydroxideHCID 86648767Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-fluoropiperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate

生成物 1

HCID 86648768cis(+/-)-2-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-fluoropiperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylic acid収率 73.1%

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
70 °C

実験手順

A 2 N aqueous lithium hydroxide solution (1.18 mL, 2.37 mmol) was added to a mixed solution of ethyl cis(±)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-fluoropiperidin-1-yl)-4-methyl-1,3-thiazole-5-carboxylate obtained in Example (196c) (105 mg, 0.237 mmol) in methanol (3 mL) and tetrahydrofuran (3 mL) at room temperature, and the mixture was stirred at 70° C. for two hours. The reaction solution was concentrated under reduced pressure. A 1 N aqueous hydrochloric acid solution (2.37 mL, 2.37 mmol) and water were added to the resulting residue, followed by extraction with ethyl acetate. The resulting organic layer was washed with water and brine, and dried over anhydrous sodium sulfate, and then the insoluble matter was separated by filtration. The filtrate was concentrated under reduced pressure to obtain 72 mg of the title compound (73%) as a colorless solid.

後処理

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. extractionfollowed by extraction with ethyl acetate
  3. washThe resulting organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe insoluble matter was separated by filtration
  6. concentrationThe filtrate was concentrated under reduced pressure

出典と根拠

ORDレコード
ord-37719abe601a4591a1c32be0b957bdf7
出典データセット
uspto-grants-2013_09
特許番号
US08536197B2

反応ノート

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