Hydrochloric Acid → HCID 67136343、化合物

HRID 230909ノート

反応式

HRID 230909 の反応式
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]2[C:14]3[C:15]([O:19][C@@H:20]4[O:37][C@H:36]([CH2:38][O:39][C:40](=[O:42])[CH3:41])[C@@H:31]([O:32][C:33](=[O:35])[CH3:34])[C@H:26]([O:27][C:28](=[O:30])[CH3:29])[C@H:21]4[O:22][C:23](=[O:25])[CH3:24])=[CH:16][CH:17]=[CH:18][C:13]=3[O:12][CH:11]=2)=[CH:4][CH:3]=1.N1C=CC=CC=1.[CH3:49][S:50](Cl)(=[O:52])=[O:51].Cl>ClCCl>[C:23]([O:22][C@@H:21]1[C@@H:26]([O:27][C:28](=[O:30])[CH3:29])[C@H:31]([O:32][C:33](=[O:35])[CH3:34])[C@@H:36]([CH2:38][O:39][C:40](=[O:42])[CH3:41])[O:37][C@H:20]1[O:19][C:15]1[C:14]2[C:10]([CH2:9][CH2:8][C:5]3[CH:4]=[CH:3][C:2]([NH:1][S:50]([CH3:49])(=[O:52])=[O:51])=[CH:7][CH:6]=3)=[CH:11][O:12][C:13]=2[CH:18]=[CH:17][CH:16]=1)(=[O:25])[CH3:24]

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 67136458HCID 67136458、化合物

生成物 1

HCID 67136343HCID 67136343、化合物

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a mixture of 3-[2-(4-aminophenyl)ethyl]-4-hydroxybenzofuran (0.3 g) and 2,3,4,6-tetra-o-acetyl-1-O-trichloroacetoimidoyl-α-D-glucopyranose (0.65 g) in dichloromethane (5 mL) was added borontrifluoride-diethyl ether complex (0.23 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution, and the resulting mixture was extracted with ethylacetate. The extract was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1-1/2-1/5) to give 3-[2-(4-aminophenyl)ethyl]-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)benzofuran (0.36 g). To a solution of the obtained 3-[2-(4-aminophenyl)ethyl]-4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)benzofuran (50 mg) in dichloromethane (3 mL) were added pyridine (0.017 mL) and methanesulfonyl chloride (0.013 mL), and the mixture was stirred at room temperature for 1 hour. The reaction mixture was poured into 0.5 mol/L hydrochloric acid, and the resulting mixture was extracted with ethyl acetate. The extract was washed with a saturated aqueous sodium hydrogen carbonate solution and brine, and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by VARIAN BOND ELUT-SCX (eluent: methanol) to give 4-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-3-[2-(4-methanesulfonylaminophenyl)ethyl]benzofuran (40 mg). This material was dissolved in methanol (3 mL). To the solution was added sodium methoxide (28% methanol solution, 0.02 mL), and the mixture was stirred at room temperature for 2 hours. The reaction mixture was concentrated under reduced pressure. To the residue was added a saturated aqueous sodium hydrogen carbonate solution, and the resulting mixture was extracted with ethylacetate. The extract was washed with brine and dried over anhydrous sodium sulfate. The solvent was removed under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=8/1) to give the title compound (19 mg).

後処理

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe extract was washed with a saturated aqueous sodium hydrogen carbonate solution and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by VARIAN BOND ELUT-SCX (eluent: methanol)

出典と根拠

ORDレコード
ord-fa8a13c3fa0b441e97bd41cb0886e0ca
出典データセット
uspto-grants-2009_07
特許番号
US07566699B2

反応ノート

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