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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
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HRID 1425424 반응식
[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]
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참가 물질

4

반응물 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

생성물 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 acid수율 41.7%

시약·촉매·용매 1

HCID 887
Methanol
용매

실험 절차

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%).

후처리

  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

출처 및 근거

ORD 기록
ord-7e3089a22f6345c8a1ed3df1c8258b38
출처 데이터셋
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08927588B2

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