Sodium Carbonate → Methyl 4'-[2-[benzyl(tert-butoxycarbonyl)amino)ethyl]-3-(isopropylamino)-4-biphenylcarboxylate

HRID 2220370ノート

反応式

HRID 2220370 の反応式
Br[C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:12][CH:13]([CH3:15])[CH3:14])[CH:3]=1.[CH2:16]([N:23]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29](B(O)O)=[CH:28][CH:27]=1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.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>[CH2:16]([N:23]([C:35]([O:37][C:38]([CH3:41])([CH3:40])[CH3:39])=[O:36])[CH2:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([NH:12][CH:13]([CH3:15])[CH3:14])[CH:3]=2)=[CH:28][CH:27]=1)[C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

参加物

8

反応物 3

HCID 10340Sodium CarbonateHCID 22171360(4-[2-[Benzyl(tert-butoxycarbonyl)amino]ethyl]phenyl]boronic acidHCID 24824349Methyl 4-bromo-2-(isopropylamino)benzoate

生成物 1

HCID 69102971Methyl 4'-[2-[benzyl(tert-butoxycarbonyl)amino)ethyl]-3-(isopropylamino)-4-biphenylcarboxylate収率 96%

試薬・触媒・溶媒 4

HCID 178418397HCID 178418397、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
70 °C

実験手順

To a solution of methyl 4-bromo-2-(isopropylamino)benzoate (433 mg) in 1,2-dimethoxyethane (6.5 ml) were added [4-[2-[benzyl(tert-butoxycarbonyl)amino]ethyl]phenyl]boronic acid (848 mg), tetrakis(triphenylphosphine)palladium (184 mg) and aqueous solution of sodium carbonate (2M, 3.5 ml), and the mixture was stirred at 70° C. for 2 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=17/3) to give methyl 4′-[2-[benzyl(tert-butoxycarbonyl)amino]ethyl]-3-(isopropylamino)-4-biphenylcarboxylate (768 mg).

後処理

  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=17/3)

出典と根拠

ORDレコード
ord-2ac86cdc741241a18611cd06c5397a94
出典データセット
uspto-grants-2008_08
特許番号
US07417060B2

反応ノート

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