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Lithium Hydroxide → 3-(4-(tert-Butoxycarbonyl)piperazin-1-yl)propanoic acid

HRID 397694
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HRID 397694 반응식
[OH-].[Li+].C([O:5][C:6](=[O:22])[CH2:7][CH2:8][N:9]1[CH2:14][CH2:13][N:12]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:11][CH2:10]1)C>C(O)C>[NH3:9].[C:18]([O:17][C:15]([N:12]1[CH2:11][CH2:10][N:9]([CH2:8][CH2:7][C:6]([OH:22])=[O:5])[CH2:14][CH2:13]1)=[O:16])([CH3:21])([CH3:19])[CH3:20]
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참가 물질

5

반응물 2

HCID 3939Lithium HydroxideHCID 23000690Tert-butyl 4-(3-ethoxy-3-oxopropyl)piperazine-1-carboxylate

생성물 2

HCID 222Ammonia수율 10%HCID 27356443-(4-(tert-Butoxycarbonyl)piperazin-1-yl)propanoic acid수율 132.2%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

1N Aqueous lithium hydroxide (15.6 ml) was added to a solution of tert-butyl 4-(3-ethoxy-3-oxopropyl)-1-piperazinecarboxylate (2.23 g) [see Preparation 89] in ethanol (95 ml). The reaction mixture was stirred for 18 hrs at room temperature, after which time the solvent was removed under reduced pressure. The crude product was purified by column chromatography on reverse phase MCI gel eluting with 1:1, acetonitrile:water and further purified on Dowex 50W-X8-100 ion-exchange resin eluting with water and then 10% ammonia to afford 3-[4-(tert-butoxycarbonyl)piperazino]propanoic acid (1.33 g) as a white solid.

후처리

  1. customafter which time the solvent was removed under reduced pressure
  2. customThe crude product was purified by column chromatography on reverse phase MCI gel
  3. washeluting with 1:1, acetonitrile
  4. customwater and further purified on Dowex 50W-X8-100 ion-exchange resin
  5. washeluting with water

출처 및 근거

ORD 기록
ord-6d7d970f34cd4be3a29bda963457bfad
출처 데이터셋
uspto-grants-2003_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06610707B1

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