Citric Acid → Sergliflozin Etabonate

HRID 2222075ノート

反応式

HRID 2222075 の反応式
[O:1]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[CH2:19][C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)[C@@H:2]1[O:10][C@H:9]([CH2:11][OH:12])[C@@H:7]([OH:8])[C@H:5]([OH:6])[C@H:3]1[OH:4].Cl[C:29]([O:31][CH2:32][CH3:33])=[O:30].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CC1C=C(C)C=C(C)N=1>[CH2:32]([O:31][C:29]([O:12][CH2:11][C@H:9]1[O:10][C@@H:2]([O:1][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:19][C:20]2[CH:21]=[CH:22][C:23]([O:26][CH3:27])=[CH:24][CH:25]=2)[C@H:3]([OH:4])[C@@H:5]([OH:6])[C@@H:7]1[OH:8])=[O:30])[CH3:33]

参加物

5

反応物 3

HCID 311Citric AcidHCID 10928Ethyl chloroformateHCID 10177526Sergliflozin

生成物 1

HCID 9824918Sergliflozin Etabonate

試薬・触媒・溶媒 1

HCID 79532,4,6-Trimethylpyridine溶媒

実験手順

To a solution of 2-(4-methoxybenzyl)phenyl β-D-glucopyranoside (0.075 g) in 2,4,6-trimethylpyridine (2 mL) was added ethyl chloroformate (0.04 mL) at room temperature. After the mixture was stirred at room temperature for 16 hours, a saturated aqueous solution of citric acid was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by preparative thin layer chromatography on silica gel (eluent:dichloromethane/methanol=10/1) to give an amorphous form of 2-(4-methoxybenzyl)phenyl 6-O-ethoxycarbonyl-β-D-glucopyranoside (0.032 g). As a result of X-ray powder diffraction analysis, the amorphous substance shows no distinct peak. 1H-NMR (CD3OD) δ ppm: 1.23 (3H, t, J=7.1 Hz), 3.30-3.65 (4H, m), 3.74 (3H, s), 3.93 (1H, d, J=15.1 Hz), 4.02 (1H, d, J=15.1 Hz), 4.05-4.20 (2H, m), 4.29 (1H, dd, J=6.4,11.7 Hz), 4.45 (1H, dd, J=2.2, 11.7 Hz), 4.89 (1H, d, J=7.4 Hz), 6.75-6.85(2H, m), 6.85-7.05 (2H, m), 7.05-7.2 (4H, m)

後処理

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe extract was washed with water
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by preparative thin layer chromatography on silica gel (eluent:dichloromethane/methanol=10/1)

出典と根拠

ORDレコード
ord-53a6749174104a6daede83aa128d0363
出典データセット
uspto-grants-2008_05
特許番号
US07371730B2

反応ノート

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