Lithium Hydroxide → 4-(1-(Naphthalen-1-ylsulfonyl)piperidin-2-yl)butanoic acid

HRID 1881685노트

반응식

HRID 1881685 반응식
[OH-].[Li+].[C:3]1([S:13]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]2[CH2:22][CH2:23][CH2:24][C:25]([O:27]C)=[O:26])(=[O:15])=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1>CO.O>[C:3]1([S:13]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH:17]2[CH2:22][CH2:23][CH2:24][C:25]([OH:27])=[O:26])(=[O:15])=[O:14])[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=1

참가 물질

4

반응물 2

HCID 3939Lithium HydroxideHCID 57904267Methyl 4-(1-(naphthalen-1-ylsulfonyl)piperidin-2-yl)butanoate

생성물 1

HCID 579041634-(1-(Naphthalen-1-ylsulfonyl)piperidin-2-yl)butanoic acid수율 91.9%

시약·촉매·용매 1

HCID 22242641Methanol--water (1/1)용매

실험 절차

Lithium hydroxide (1.58 g, 65.9 mmol) was added to a solution of methyl 4-(1-(naphthalene-1-ylsulfonyl)piperidine-2-yl)butanoate 3 (4.95 g, 13.18 mmol) in methanol/water (54 ml/36 ml) and the reaction mixture was stirred at room temperature overnight. The completeness of the reaction was checked by means of TLC. When the reaction was complete, the methanol was distilled off under reduced pressure and ethyl acetate was added to the residue. The mixture was acidified with dilute HCl. The aqueous phase was extracted 2× with ethyl acetate and the combined organic phases were dried over Na2SO4 and concentrated under reduced pressure to obtain the desired product 4-(1-(naphthalene-1-ylsulfonyl)piperidine-2-yl)butanoic acid (AC-21) (4.38 g, 91%).

후처리

  1. distillationthe methanol was distilled off under reduced pressure and ethyl acetate
  2. additionwas added to the residue
  3. extractionThe aqueous phase was extracted 2× with ethyl acetate
  4. dry with materialthe combined organic phases were dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-cde0d2e1b6a446cbb2e83ad3f06f7d78
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08318769B2

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