(L)-ethyl lactate → 2-{[4-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-2-methyl-but-2-enyloxymethyl]-phenoxy-phosphinoyloxy}-propionic Acid Ethyl Ester

HRID 33639

반응식

HRID 33639 반응식
[C:1]1([O:7][P:8]([CH2:11][O:12][CH2:13][C:14]([CH3:31])=[CH:15][CH2:16][C:17]2[C:18]([OH:30])=[C:19]3[C:23](=[C:24]([CH3:28])[C:25]=2[O:26][CH3:27])[CH2:22][O:21][C:20]3=[O:29])(=[O:10])[OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:32]([O:37][CH2:38][CH3:39])(=[O:36])[C@H:33]([CH3:35])O.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F>N1C=CC=CC=1>[CH2:38]([O:37][C:32](=[O:36])[CH:33]([O:10][P:8]([CH2:11][O:12][CH2:13][C:14]([CH3:31])=[CH:15][CH2:16][C:17]1[C:18]([OH:30])=[C:19]2[C:23](=[C:24]([CH3:28])[C:25]=1[O:26][CH3:27])[CH2:22][O:21][C:20]2=[O:29])([O:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)=[O:9])[CH3:35])[CH3:39]

참가 물질

5

반응물 3

HCID 92831(L)-ethyl lactateHCID 2724699PyBOP2회HCID 76541028[4-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-2-methyl-but-2-enyloxymethyl]-phosphonic acid monophenyl ester

생성물 1

HCID 725636462-{[4-(4-Hydroxy-6-methoxy-7-methyl-3-oxo-1,3-dihydro-isobenzofuran-5-yl)-2-methyl-but-2-enyloxymethyl]-phenoxy-phosphinoyloxy}-propionic Acid Ethyl Ester수율 34.2%

시약·촉매·용매 1

HCID 1049Pyridine용매

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-enyloxymethyl]-phosphonic acid monophenyl ester (18.5 mg, 0.040 mmol) and ethyl (S)-(−)-lactate (47 μL, 0.400 mmol) in pyridine (0.5 mL) was added PyBOP (32 mg, 0.060 mmol). The solution was stirred at room temperature for 1 hour, when an additional portion of PyBOP (21 mg, 0.040 mmol) was added. The solution was stirred for another hour and concentrated. The residue was purified by HPLC to provide 7.5 mg of the desired product as a clear oil. 1H NMR (300 MHz, CD3OD) δ 1.22 and 1.25 (t, 3H, J=7 Hz), 1.42 and 1.50 (d, 3H, J=7 Hz), 1.82 and 1.83 (s, 3H), 2.16 (s, 3H), 3.47 (d, 2H, J=7 Hz), 3.78 (s, 3H), 3.89 (d, 1H, J=8 Hz), 3.93-4.02 (m, 3H), 4.10-4.22 (m, 2H), 4.94-5.08 (m, 1H), 5.25 (s, 2H), 5.50-5.60 (m, 1H), 7.15-7.27 (m, 3H), 7.33-7.41 (m, 2H) ppm; 31P (121.4 MHz, CD3OD) δ 18.9, 20.3 ppm (diastereomers at phosphorus); MS (m/z) 549.2 [M+H]+, 571.3 [M+Na]+.

후처리

  1. stirringThe solution was stirred for another hour
  2. concentrationconcentrated
  3. customThe residue was purified by HPLC

출처 및 근거

ORD 기록
ord-5c9b7603e87d4499a95653c268512fff
출처 데이터셋
uspto-grants-2008_09
특허 번호
US07429565B2

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