Sodium Bicarbonate → 5-(N,N-dimethylaminocarbonyl)-2-methoxyphenylboronic acid

HRID 604221ノート

反応式

HRID 604221 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](O)=[O:10])=[CH:5][C:4]=1[B:12]([OH:14])[OH:13].[CH3:15][NH:16][CH3:17].O1CCCC1.O.O.ON1C2C=CC=CC=2N=N1.Cl.C(N=C=NCCCN(C)C)C.C(=O)(O)[O-].[Na+]>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9](=[O:10])[N:16]([CH3:17])[CH3:15])=[CH:5][C:4]=1[B:12]([OH:14])[OH:13]

参加物

7

反応物 5

HCID 516892Sodium BicarbonateHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 22320367Dimethylamine tetrahydrofuranHCID 426145415-Carboxy-2-methoxybenzeneboronic acidHCID 666034961-Hydroxybenzotriazole dihydrate

生成物 1

HCID 575560785-(N,N-dimethylaminocarbonyl)-2-methoxyphenylboronic acid

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

The crude 2-methoxy-5-carboxyphenylboronic acid (370 mg) is dissolved in N,N-dimethylformamide (10 ml), and thereto are added 2.0M-dimethylamine/tetrahydrofuran solution (1.9 ml), 1-hydroxybenzotriazole dihydrate (725 mg), 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (579 mg). The mixture is stirred at room temperature for 3 hours, and thereto is added a saturated aqueous sodium bicarbonate solution, and the mixture is extracted with ethyl acetate twice. The organic layer is dried over magnesium sulfate and concentrated under reduced pressure. The resulting residue is purified by silica gel column chromatography (chloroform:methanol=19:1) to give 2-methoxy-5-dimethylcarbamoylphenylboronic acid (210 mg). MS (m/z): 224 [M+H]+

後処理

  1. extractionthe mixture is extracted with ethyl acetate twice
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resulting residue is purified by silica gel column chromatography (chloroform:methanol=19:1)

出典と根拠

ORDレコード
ord-45ee4f0adaba4e47922a3b5225b7b712
出典データセット
uspto-grants-2011_03
特許番号
US07906517B2

反応ノート

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