Sodium Hydroxide → 3-(beta-d-Glucopyranosyloxy)-4-[(4-methylthiophenyl)methyl]-1h-pyrazole

HRID 2102319

反応式

HRID 2102319 の反応式
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][C:10]2[C:11](=[O:21])[NH:12][NH:13][C:14]=2C2C=CC=CC=2)=[CH:5][CH:4]=1.CC([O:25][CH2:26][C@H:27]1[O:32][C@H:31](Br)[C@H:30]([O:34]C(C)=O)[C@@H:29]([O:38]C(C)=O)[C@@H:28]1[O:42]C(C)=O)=O.[OH-].[Na+]>[Br-].C([N+](CCCC)(CCCC)CCCC)C1C=CC=CC=1.ClCCl>[C@@H:31]1([O:21][C:11]2[C:10]([CH2:9][C:6]3[CH:5]=[CH:4][C:3]([S:2][CH3:1])=[CH:8][CH:7]=3)=[CH:14][NH:13][N:12]=2)[O:32][C@H:27]([CH2:26][OH:25])[C@@H:28]([OH:42])[C@H:29]([OH:38])[C@H:30]1[OH:34]

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 101776alpha-D-Glucopyranosyl bromide, tetraacetateHCID 669710624-[(4-Methylthiophenyl)methyl]-5-phenyl-1,2-dihydro-3h-pyrazole-3-one

生成物 1

HCID 1785031463-(beta-d-Glucopyranosyloxy)-4-[(4-methylthiophenyl)methyl]-1h-pyrazole収率 29.4%

試薬・触媒・溶媒 2

HCID 2724282Benzenemethanaminium, N,N,N-tributyl-, bromide触媒HCID 6344Dichloromethane溶媒

実験手順

To a suspension of 4-[(4-methylthiophenyl)methyl]-5-phenyl-1,2-dihydro-3H-pyrazole-3-one (0.087 g), acetobromo-α-D-glucose (0.62 g) and benzyltri(n-butyl)ammonium bromide (0.054 g) in dichloromethane (3 mL) was added a sodium hydroxide aqueous solution (5 mol/L, 0.9 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent: tetrahydrofuran). The obtained semi purified 4-[(4-methylthiophenyl)methyl]-3-(2,3,4,6-tetraacethyl-β-D-glucopyranosyloxy)-1H-pyrazole was dissolved in methanol (5 mL), and sodium methoxide (28% methanol solution, 0.28 mL) was added to the solution. The mixture was stirred at room temperature for 2 hours. Acetic acid (0.090 g) was added to the reaction mixture, and the solvent was removed. Water (5 mL) was added to the residue, and the mixture was purified by solid phase extraction on ODS (washing solvent: water/methanol=5/1, eluent: methanol). Column chromatography on silica gel (eluent: dichloromethane/methanol=20/1-7/1) was used for further purification to give the title compound (0.033 g).

後処理

  1. customThe reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent: tetrahydrofuran)
  2. customThe obtained semi purified 4-[(4-methylthiophenyl)methyl]-3-(2,3,4,6-tetraacethyl-β-D-glucopyranosyloxy)-1H-pyrazole
  3. dissolutionwas dissolved in methanol (5 mL)
  4. additionsodium methoxide (28% methanol solution, 0.28 mL) was added to the solution
  5. stirringThe mixture was stirred at room temperature for 2 hours
  6. additionAcetic acid (0.090 g) was added to the reaction mixture
  7. customthe solvent was removed
  8. additionWater (5 mL) was added to the residue
  9. customthe mixture was purified by solid phase extraction on ODS (washing solvent: water/methanol=5/1, eluent: methanol)
  10. customColumn chromatography on silica gel (eluent: dichloromethane/methanol=20/1-7/1) was used for further purification

出典と根拠

ORDレコード
ord-123539307f5a47ba9d770d4f37f6024a
出典データセット
uspto-grants-2009_08
特許番号
US07576063B2

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