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Lithium Hydroxide → trans-1-[Bis(4-methoxyphenyl)methyl]-6-oxo-4-(2,4,5-trifluorophenyl)piperidine-3-carboxylic acid

HRID 2237756
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인쇄 미리보기

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HRID 2237756 반응식
C[O:2][C:3]([C@H:5]1[C@H:10]([C:11]2[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=2[F:19])[CH2:9][C:8](=[O:20])[N:7]([CH:21]([C:30]2[CH:35]=[CH:34][C:33]([O:36][CH3:37])=[CH:32][CH:31]=2)[C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[CH2:6]1)=[O:4].[OH-].[Li+]>O1CCCC1.CO>[CH3:29][O:28][C:25]1[CH:26]=[CH:27][C:22]([CH:21]([C:30]2[CH:31]=[CH:32][C:33]([O:36][CH3:37])=[CH:34][CH:35]=2)[N:7]2[C:8](=[O:20])[CH2:9][C@@H:10]([C:11]3[CH:16]=[C:15]([F:17])[C:14]([F:18])=[CH:13][C:12]=3[F:19])[C@H:5]([C:3]([OH:4])=[O:2])[CH2:6]2)=[CH:23][CH:24]=1
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참가 물질

4

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HCID 3939Lithium HydroxideHCID 86617465Methyl-trans-1-[bis(4-methoxyphenyl)methyl]-6-oxo-4-(2,4,5-trifluorophenyl)piperidine-3-carboxylate

생성물 1

HCID 67201019trans-1-[Bis(4-methoxyphenyl)methyl]-6-oxo-4-(2,4,5-trifluorophenyl)piperidine-3-carboxylic acid

시약·촉매·용매 1

HCID 21899815MeOH tetrahydrofuran용매

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온도
60 °C

실험 절차

To a solution of 5.9 g (11.5 mmol) of the product from Step D in 100 mL of 3:1 tetrahydrofuran/methanol was added 30 mL (30 mmol) of a 1N aqueous lithium hydroxide solution and the resulting mixture was stirred at 60° C. for 2 h. The solution was concentrated and acidified with 100 mL of 1N aqueous hydrochloric acid. The resulting mixture was then extracted with three 250-mL portions of ethyl acetate, and the organic phases combined and washed sequentially with 1N hydrochloric acid and saturated aqueous brine (100 mL each). The organic phase was dried over magnesium sulfate, filtered, and evaporated in vacuo to yield the title acid as a colorless foamy solid that was used without further purification. LC/MS 522.2 (M+23).

후처리

  1. concentrationThe solution was concentrated
  2. extractionThe resulting mixture was then extracted with three 250-mL portions of ethyl acetate
  3. washwashed sequentially with 1N hydrochloric acid and saturated aqueous brine (100 mL each)
  4. dry with materialThe organic phase was dried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated in vacuo

출처 및 근거

ORD 기록
ord-37c1d13a9aac4c16b7e578d2777da961
출처 데이터셋
uspto-grants-2010_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07718667B2

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