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Sodium Carbonate → Methyl 1-[4-(2-nitrobenzenesulfonyl)-piperazin-1-yl]-cyclopropanecarboxylate

HRID 1961679
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인쇄 미리보기

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HRID 1961679 반응식
FC(F)(F)S(O[CH2:7][CH2:8][N:9]([CH2:22][CH2:23]OS(C(F)(F)F)(=O)=O)[S:10]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[N+:19]([O-:21])=[O:20])(=[O:12])=[O:11])(=O)=O.Cl.[NH2:35][C:36]1([C:39]([O:41][CH3:42])=[O:40])[CH2:38][CH2:37]1.C(=O)([O-])[O-].[Na+].[Na+]>C(#N)C.C(OCC)(=O)C>[N+:19]([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=1[S:10]([N:9]1[CH2:8][CH2:7][N:35]([C:36]2([C:39]([O:41][CH3:42])=[O:40])[CH2:38][CH2:37]2)[CH2:23][CH2:22]1)(=[O:11])=[O:12])([O-:21])=[O:20]
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참가 물질

6

반응물 3

HCID 10340Sodium CarbonateHCID 12760695Methyl 1-aminocyclopropane-1-carboxylate hydrochlorideHCID 86601384N,N-Bis-(2-trifluoromethanesulfonyloxyethyl)-2-nitrobenzenesulfonamide

생성물 1

HCID 66628127Methyl 1-[4-(2-nitrobenzenesulfonyl)-piperazin-1-yl]-cyclopropanecarboxylate

시약·촉매·용매 2

HCID 6342Acetonitrile용매
HCID 8857Ethyl Acetate용매

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온도
60 °C

실험 절차

A solution of N,N-bis-(2-trifluoromethanesulfonyloxyethyl)-2-nitrobenzenesulfonamide (1.83 g, 3.30 mmol) from Example 16B and methyl 1-aminocyclopropane-1-carboxylate HCl (0.50 g, 3.30 mmol) in anhydrous acetonitrile (10 mL) was treated with sodium carbonate (1.40 g, 13.2 mmol) and heated overnight at 60° C. (J. A. Kozlowski, et al., Bioorg. Med. Chem. Lett. 12: 791-794, 2002). Reaction diluted with ethyl acetate, washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. The residue was purified by normal phase HPLC on a Biotage pre-packed silica gel column eluting with 3:1 hexane:ethyl acetate to afford the title compound. MS (ESI) m/z 370 (M+H)+.

후처리

  1. customReaction
  2. washwashed with water and brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by normal phase HPLC on a Biotage pre-packed silica gel column
  7. washeluting with 3:1 hexane

출처 및 근거

ORD 기록
ord-2ed7f7e8ef1347c2bf1c73416a546082
출처 데이터셋
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08415354B2

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