2,6-Lutidine → [4-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-2-methyl-but-2-enyl]-phosphonic Acid

HRID 33638

반응식

HRID 33638 반응식
C[O:2][P:3]([CH2:7][C:8]([CH3:25])=[CH:9][CH2:10][C:11]1[C:12]([OH:24])=[C:13]2[C:17](=[C:18]([CH3:22])[C:19]=1[O:20][CH3:21])[CH2:16][O:15][C:14]2=[O:23])(=[O:6])[O:4]C.C[Si](Br)(C)C.N1C(C)=CC=CC=1C>C(#N)C>[OH:24][C:12]1[C:11]([CH2:10][CH:9]=[C:8]([CH3:25])[CH2:7][P:3](=[O:2])([OH:6])[OH:4])=[C:19]([O:20][CH3:21])[C:18]([CH3:22])=[C:17]2[C:13]=1[C:14](=[O:23])[O:15][CH2:16]2

참가 물질

5

반응물 3

HCID 79372,6-LutidineHCID 76113BromotrimethylsilaneHCID 75023209[4-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-2-methyl-but-2-enyl]-phosphonic Acid Dimethyl Ester

생성물 1

HCID 67010405[4-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-2-methyl-but-2-enyl]-phosphonic Acid수율 73%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

실험 절차

To a solution of [4-(4-hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-2-methyl-but-2-enyl]-phosphonic acid dimethyl ester (18 mg, 0.049 mmol) in acetonitrile (2 mL) was added TMSBr (63 μL, 0.49 mmol) and 2,6-lutidine (85 μL, 0.73 mmol) at 0° C. The reaction solution was allowed to warm to room temperature and stirred for 2 hours when completion of the reaction was observed by LCMS. The reaction was cooled to 0° C. and quenched by the addition of MeOH. The reaction mixture was concentrated under reduced pressure and the residue was purified by RP HPLC using a C18 column with a gradient of H2O-acetonitrile (5-0%) over 20 minutes to provide 12.2 mg (73%) of the product. 1H NMR (300 MHz, CD3OD) δ 1.95 (s, 3H), 2.15 (s, 3H), 2.48 (d, 2H, J=22 Hz), 3.44 (t, 2H, J=6 Hz), 3.79 (s, 3H), 5.24 (s, 2H),5.38 (q, 1H, J=7 Hz), 6.87 (br s, 1H) ppm; MS (m/z) 341 [M−H]−.

후처리

  1. temperatureThe reaction was cooled to 0° C.
  2. customquenched by the addition of MeOH
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customthe residue was purified by RP HPLC
  5. customover 20 minutes

출처 및 근거

ORD 기록
ord-1a2408d56522456f86f3266a45b5247e
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429565B2

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