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

HRID 604221노트

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HRID 604221 반응식
[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]

참가 물질

7

반응물 5

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

생성물 1

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

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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]+

후처리

  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)

출처 및 근거

ORD 기록
ord-45ee4f0adaba4e47922a3b5225b7b712
출처 데이터셋
uspto-grants-2011_03
특허 번호
US07906517B2

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