Pentane → 1-tert-Butoxycarbonyl-4-[[(2RS)-2-(6-chloropyridin-3-yl)-2-hydroxyethyl]sulfonyl]piperazine

HRID 1061050노트

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HRID 1061050 반응식
[C:1]([O:5][C:6]([N:8]1[CH2:13][CH2:12][N:11]([S:14]([CH3:17])(=[O:16])=[O:15])[CH2:10][CH2:9]1)=[O:7])([CH3:4])([CH3:3])[CH3:2].C([Li])(C)(C)C.CCCCC.[Cl:28][C:29]1[CH:36]=[CH:35][C:32]([CH:33]=[O:34])=[CH:31][N:30]=1>O1CCCC1.C(OCC)(=O)C.C(O)(C)C>[C:1]([O:5][C:6]([N:8]1[CH2:9][CH2:10][N:11]([S:14]([CH2:17][CH:33]([C:32]2[CH:31]=[N:30][C:29]([Cl:28])=[CH:36][CH:35]=2)[OH:34])(=[O:15])=[O:16])[CH2:12][CH2:13]1)=[O:7])([CH3:4])([CH3:3])[CH3:2]

참가 물질

8

반응물 4

HCID 8003PentaneHCID 27640536-Chloropyridine-3-carbaldehydeHCID 4496004Tert-butyl 4-(methylsulfonyl)piperazine-1-carboxylateHCID 178418306HCID 178418306, 화합물

생성물 1

HCID 227095471-tert-Butoxycarbonyl-4-[[(2RS)-2-(6-chloropyridin-3-yl)-2-hydroxyethyl]sulfonyl]piperazine

시약·촉매·용매 3

HCID 3776Isopropanol용매HCID 8028Tetrahydrofuran용매2회HCID 8857Ethyl Acetate용매

실험 절차

In tetrahydrofuran (8 ml), 1-tert-butoxycarbonyl-4-methanesulfonylpiperazine (838 mg) was dissolved, followed by the addition of tert-butyl lithium (a 1.7M pentane solution, 1.72 ml) at −78° C. in an argon gas atmosphere. The resulting mixture was stirred for 2 hours. After the dropwise addition of a solution of 6-chloronicotinaldehyde (346 mg) in tetrahydrofuran (tetrahydrofuran: 4 ml) and stirring at −78° C. for 3 hours, the reaction mixture was added with isopropanol (1 ml). The resulting mixture was heated to room temperature and diluted with ethyl acetate. The diluted solution was washed with water and saturated saline and dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was recrystallized from ethyl acetate, whereby the title compound (532 mg, 54%) was obtained.

후처리

  1. stirringstirring at −78° C. for 3 hours
  2. washThe diluted solution was washed with water and saturated saline
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe residue obtained
  5. distillationby distilling off the solvent under reduced pressure
  6. customwas recrystallized from ethyl acetate, whereby the title compound (532 mg, 54%)
  7. customwas obtained

출처 및 근거

ORD 기록
ord-313ee3bad9064d41853f8026d0e6120e
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06525042B1

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