N-methyliminodiacetic acid → 2-(4-(4-Fluorophenethoxy)phenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione

HRID 718371

반응식

HRID 718371 반응식
[F:1][C:2]1[CH:19]=[CH:18][C:5]([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([B:15]([OH:17])[OH:16])=[CH:11][CH:10]=2)=[CH:4][CH:3]=1.[CH3:20][N:21]([CH2:26][C:27](O)=[O:28])[CH2:22][C:23](O)=[O:24]>C1(C)C=CC=CC=1.CS(C)=O.CCOC(C)=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][CH2:7][O:8][C:9]2[CH:14]=[CH:13][C:12]([B:15]3[O:17][C:27](=[O:28])[CH2:26][N:21]([CH3:20])[CH2:22][C:23](=[O:24])[O:16]3)=[CH:11][CH:10]=2)=[CH:18][CH:19]=1

참가 물질

6

반응물 2

HCID 20441N-methyliminodiacetic acidHCID 123643410(4-(4-Fluorophenethoxy)phenyl)boronic acid

생성물 1

HCID 1317341662-(4-(4-Fluorophenethoxy)phenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione수율 75.5%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

실험 절차

A slurry of (4-(4-fluorophenethoxy)phenyl)boronic acid (122 g, 469 mmol) and 2,2′-(methylazanediyl)diacetic acid (76 g, 516 mmol) in anhydrous toluene (500 mL) and DMSO (200 mL) was refluxed for 4 h. Then, cooled, diluted with EtOAc (500 mL), washed with water (5×200 mL), brine (2×100 mL), dried (MgSO4), filtered and concentrated to give light orange foam which was purified by flash chromatography using 5-40% acetone/CH2Cl2 (5% increment per 2-lit) to afford 2-(4-(4-fluorophenethoxy)phenyl)-6-methyl-1,3,6,2-dioxazaborocane-4,8-dione (131.38 g, 354 mmol, 75% yield) as white solid. 1H NMR (500 MHz, CDCl3) δ 7.43 (d, J=8.4 Hz, 2H), 7.28-7.24 (m, 2H), 7.04-6.99 (m, 2H), 6.92 (d, J=8.5 Hz, 2H), 4.17 (t, J=6.9 Hz, 2H), 4.00 (d, J=16.6 Hz, 2H), 3.76 (d, J=16.6 Hz, 2H), 3.08 (t, J=6.8 Hz, 2H), 2.54 (s, 3H). LCMS (M+H)=372.3.

후처리

  1. temperatureThen, cooled
  2. washwashed with water (5×200 mL), brine (2×100 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customto give light orange foam which
  7. customwas purified by flash chromatography

출처 및 근거

ORD 기록
ord-08268ea527864686b0cb7d3da43ecca2
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09193720B2

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