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

HRID 1365029

반응식

HRID 1365029 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 2724282Benzenemethanaminium, N,N,N-tributyl-, bromide촉매HCID 6344Dichloromethane용매

실험 절차

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-methyl-thiophenyl)methyl]-3-(2,3,4,6-tetraacethyl-β-D-gluco-pyranosyloxy)-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).

후처리

  1. customThe reaction mixture was purified by column chromatography on aminopropylated silica gel (eluent: tetrahydrofuran)
  2. customThe obtained semi purified 4-[(4-methyl-thiophenyl)methyl]-3-(2,3,4,6-tetraacethyl-β-D-gluco-pyranosyloxy)-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

출처 및 근거

ORD 기록
ord-5eb3aa8ffe6c4ef2a29bb2b2d433bb83
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07888487B2

연결된 노트

불러오는 중…