Sodium Carbonate → Methyl 4'-[2-[benzyl(tert-butoxycarbonyl)amino]ethyl]-2-nitro-4-biphenylcarboxylate

HRID 2220394노트

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HRID 2220394 반응식
[CH2:1]([N:8]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14](B(O)O)=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[N+:27]([C:30]1[CH:31]=[C:32]([CH:37]=[CH:38][C:39]=1OS(C(F)(F)F)(=O)=O)[C:33]([O:35][CH3:36])=[O:34])([O-:29])=[O:28].C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(OCC)(=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([N:8]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([C:39]2[CH:38]=[CH:37][C:32]([C:33]([O:35][CH3:36])=[O:34])=[CH:31][C:30]=2[N+:27]([O-:29])=[O:28])=[CH:13][CH:12]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

8

반응물 3

HCID 10340Sodium CarbonateHCID 10925511Methyl 3-nitro-4-[[(trifluoromethyl)sulfonyl]oxy]benzoateHCID 22171360(4-[2-[Benzyl(tert-butoxycarbonyl)amino]ethyl]phenyl]boronic acid

생성물 1

HCID 69104049Methyl 4'-[2-[benzyl(tert-butoxycarbonyl)amino]ethyl]-2-nitro-4-biphenylcarboxylate수율 71.2%

시약·촉매·용매 4

HCID 178418397HCID 178418397, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매HCID 8857Ethyl Acetate용매

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온도
80 °C

실험 절차

To a solution of [4-[2-[benzyl(tert-butoxycarbonyl)amino]ethyl]phenyl]boronic acid (3.1 g) in 1,2-dimethoxyethane (45 ml) were added methyl 3-nitro-4-[[(trifluoromethyl)sulfonyl]oxy]benzoate (3.0 g), tetrakis(triphenylphosphine)palladium (800 mg) and aqueous solution of sodium carbonate (2M, 9.1 ml), and the mixture was stirred at 80° C. for 4 hours under nitrogen. The mixture was diluted with ethyl acetate and water. The organic layer was separated, washed with brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3/1) to give methyl 4′-[2-[benzyl(tert-butoxycarbonyl)amino]ethyl]-2-nitro-4-biphenylcarboxylate (3.05 g).

후처리

  1. customThe organic layer was separated
  2. washwashed with brine
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane/ethyl acetate=3/1)

출처 및 근거

ORD 기록
ord-a729ae6c697149a38d30fc19474baa3c
출처 데이터셋
uspto-grants-2008_08
특허 번호
US07417060B2

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