Ethoxyacetic acid → 2'-(6-O-ethoxyacetyl-beta-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)propiophenone

HRID 355349

반응식

HRID 355349 반응식
[C@@H:1]1([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[C:14]=2[C:20](=[O:32])[CH2:21][CH2:22][C:23]2[CH:31]=[CH:30][C:26]3[O:27][CH:28]=[CH:29][C:25]=3[CH:24]=2)[O:9][C@H:8]([CH2:10][OH:11])[C@@H:6]([OH:7])[C@H:4]([OH:5])[C@H:2]1[OH:3].[CH2:33]([O:35][CH2:36][C:37](O)=[O:38])[CH3:34].C1N(P(Cl)(N2C(=O)OCC2)=O)C(=O)OC1.C(=O)([O-])O.[Na+]>N1C=CC=CC=1.C(Cl)(Cl)Cl>[CH2:33]([O:35][CH2:36][C:37]([O:11][CH2:10][C@H:8]1[O:9][C@@H:1]([O:12][C:13]2[CH:18]=[CH:17][CH:16]=[C:15]([OH:19])[C:14]=2[C:20](=[O:32])[CH2:21][CH2:22][C:23]2[CH:31]=[CH:30][C:26]3[O:27][CH:28]=[CH:29][C:25]=3[CH:24]=2)[C@H:2]([OH:3])[C@@H:4]([OH:5])[C@@H:6]1[OH:7])=[O:38])[CH3:34]

참가 물질

7

반응물 4

HCID 12301Ethoxyacetic acidHCID 152842Bis(2-oxo-3-oxazolidinyl)phosphinic chlorideHCID 516892Sodium BicarbonateHCID 99331252'-(beta-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)propiophenone

생성물 1

HCID 106022782'-(6-O-ethoxyacetyl-beta-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)propiophenone수율 35.5%

시약·촉매·용매 2

HCID 1049Pyridine용매HCID 6212Chloroform용매

실험 절차

To a solution of 2'-(β-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)propiophenone (889 mg) and ethoxyacetic acid (250 mg) in pyridine (25 ml) is added N,N-bis(2-oxo-3-oxazolidinyl)phosphinic chloride (1527 mg) under ice-cooling, and the mixture is stirred at room temperature for 19 hours. To the reaction solution are added a saturated aqueous sodium hydrogen carbonate solution and chloroform, and the mixture is stirred. The organic layer is collected, washed with water, dried, and evaporated to remove the solvent. The residue is dissolved in a mixture of methanol (10 ml) and tetrahydrofuran (10 ml), and thereto is added triethylamine (202 mg). The mixture is stirred at 50° C. for 40 minutes, and evaporated to remove the solvent. The residue is dissolved in ethyl acetate, and the mixture is washed with water, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform/methanol) to give 2'-(6-O-ethoxyacetyl-β-D-glucopyranosyloxy)-6'-hydroxy-3-(5-benzo[b]furanyl)propiophenone (377 mg).

후처리

  1. temperaturecooling
  2. stirringthe mixture is stirred
  3. customThe organic layer is collected
  4. washwashed with water
  5. customdried
  6. customevaporated
  7. customto remove the solvent
  8. dissolutionThe residue is dissolved in a mixture of methanol (10 ml) and tetrahydrofuran (10 ml)
  9. additionis added triethylamine (202 mg)
  10. stirringThe mixture is stirred at 50° C. for 40 minutes
  11. customevaporated
  12. customto remove the solvent
  13. dissolutionThe residue is dissolved in ethyl acetate
  14. washthe mixture is washed with water
  15. customdried
  16. customevaporated
  17. customto remove the solvent
  18. customThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol)

출처 및 근거

ORD 기록
ord-464c576ba4d94c758cbc5996942a984c
출처 데이터셋
uspto-grants-1998_11
특허 번호
US05830873

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