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Lithium Hydroxide → cis(+/-)-2-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-4-[(2-fluoroethyl)carbamoyl]-1,3-thiazole-5-carboxylic acid

HRID 1425424
ノート
印刷プレビュー

反応式

HRID 1425424 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:31]([O:33]CC)=[O:32])=[C:23]([C:25](=[O:30])[NH:26][CH2:27][CH2:28][F:29])[N:24]=3)[CH2:16][C@H:15]2[O:36][CH2:37][CH3:38])=[O:12])[NH:7][C:8]=1[CH2:9][CH3:10]>CO>[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:31]([OH:33])=[O:32])=[C:23]([C:25](=[O:30])[NH:26][CH2:27][CH2:28][F:29])[N:24]=3)[CH2:16][C@H:15]2[O:36][CH2:37][CH3:38])=[O:12])[NH:7][C:8]=1[CH2:9][CH3:10]
参加物実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 3939Lithium HydroxideHCID 86648837Ethyl cis(+/-)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-4-[(2-fluoroethyl)carbamoyl]-1,3-thiazole-5-carboxylate

生成物 1

HCID 86648838cis(+/-)-2-(4-{[(4-Chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-4-[(2-fluoroethyl)carbamoyl]-1,3-thiazole-5-carboxylic acid収率 41.7%

試薬・触媒・溶媒 1

HCID 887
Methanol
溶媒

実験手順

A 2 N aqueous lithium hydroxide solution (1.92 mL, 3.83 mmol) was added to a solution of ethyl cis(±)-2-(4-{[(4-chloro-5-ethyl-1H-imidazol-2-yl)carbonyl]amino}-3-ethoxypiperidin-1-yl)-4-[(2-fluoroethyl)carbamoyl]-1,3-thiazole-5-carboxylate obtained in Example (250a) (209 mg, 0.38 mmol) in methanol (4 mL) at room temperature, followed by stirring for 4.5 hours. The reaction solution was concentrated under reduced pressure, and then a 1 N aqueous hydrochloric acid solution was added to the resulting residue. The aqueous layer was extracted with ethyl acetate. The combined organic layers were dried over anhydrous magnesium sulfate and filtered, and then the filtrate was concentrated under reduced pressure. The resulting solid was suspended and washed in diethyl ether to obtain 82 mg of the title compound as a milk white solid (41%).

後処理

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additiona 1 N aqueous hydrochloric acid solution was added to the resulting residue
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate was concentrated under reduced pressure
  7. washwashed in diethyl ether

出典と根拠

ORDレコード
ord-7e3089a22f6345c8a1ed3df1c8258b38
出典データセット
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08927588B2

反応ノート

読み込み中…

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