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3-(2-Carboxyethyl)phenylboronic acid → 3-[2'-(1-tert-Butoxycarbonylamino-ethyl)-5'-(pyridin-4-ylcarbamoyl)-biphenyl-3-yl]-propionic acid

HRID 2409365
ノート
印刷プレビュー

反応式

HRID 2409365 の反応式
[C:1]([O:5][C:6](=[O:26])[NH:7][CH:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:24])[NH:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:12][C:11]=1Br)[CH3:9])([CH3:4])([CH3:3])[CH3:2].[C:27]([CH2:30][CH2:31][C:32]1[CH:33]=[C:34](B(O)O)[CH:35]=[CH:36][CH:37]=1)([OH:29])=[O:28]>COCCOC.CCO.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>[C:1]([O:5][C:6]([NH:7][CH:8]([C:10]1[CH:15]=[CH:14][C:13]([C:16](=[O:24])[NH:17][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)=[CH:12][C:11]=1[C:34]1[CH:35]=[CH:36][CH:37]=[C:32]([CH2:31][CH2:30][C:27]([OH:29])=[O:28])[CH:33]=1)[CH3:9])=[O:26])([CH3:4])([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

5

反応物 2

HCID 38561183-(2-Carboxyethyl)phenylboronic acidHCID 67408319{1-[2-Bromo-4-(pyridine-4-ylcarbamoyl)-phenyl]-ethyl}-carbamic acid tert-butyl ester

生成物 1

HCID 674223603-[2'-(1-tert-Butoxycarbonylamino-ethyl)-5'-(pyridin-4-ylcarbamoyl)-biphenyl-3-yl]-propionic acid

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒
HCID 20074477
Dimethoxyethane ethanol
溶媒

反応条件

温度
160 °C

実験手順

To a solution of {1-[2-bromo-4-(pyridine-4-ylcarbamoyl)-phenyl]-ethyl}-carbamic acid tert-butyl ester (3122 μmol) in a mixture of DME/EtOH/2N Na2CO3: 1/1/1 (20 ml) were added 3-carboxyethylphenylboronic acid (1.5 eq) and Pd tetrakis (0.05 eq). The reaction mixture was heated in the microwave at 160° C. for 15 minutes. The reaction mixture was cooled to RT, filtered over celite and washed with EtOAc and MeOH. The solvents were removed under reduced pressure. The compound was purified by column chromatography (silicagel, DCM/MeOH gradient).

後処理

  1. temperatureThe reaction mixture was cooled to RT
  2. filtrationfiltered over celite
  3. washwashed with EtOAc and MeOH
  4. customThe solvents were removed under reduced pressure
  5. customThe compound was purified by column chromatography (silicagel, DCM/MeOH gradient)

出典と根拠

ORDレコード
ord-d0257c6fe70e48c58378d16c13d245ca
出典データセット
uspto-grants-2014_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08815873B2

反応ノート

読み込み中…

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