Hydrochloric Acid → HCID 68944549, compound

HRID 2189406Notes

Reaction equation

HRID 2189406 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:8]([CH:9]([CH3:11])[CH3:10])=[C:7]([CH2:12][C:13]2[CH:18]=[CH:17][C:16]([OH:19])=[CH:15][C:14]=2[CH3:20])[C:6]([O:21][C@@H:22]2[O:48][C@H:47]([CH2:49][O:50][C:51](=[O:56])[C:52]([CH3:55])([CH3:54])[CH3:53])[C@@H:39]([O:40][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])[C@H:31]([O:32][C:33](=[O:38])[C:34]([CH3:37])([CH3:36])[CH3:35])[C@H:23]2[O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[N:5]1.Br[CH2:58][CH2:59][CH2:60][Cl:61].[OH-].[Na+].Cl>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.O1CCCC1>[Cl:61][CH2:60][CH2:59][CH2:58][O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][C:7]2[C:6]([O:21][C@@H:22]3[O:48][C@H:47]([CH2:49][O:50][C:51](=[O:56])[C:52]([CH3:54])([CH3:53])[CH3:55])[C@@H:39]([O:40][C:41](=[O:46])[C:42]([CH3:45])([CH3:44])[CH3:43])[C@H:31]([O:32][C:33](=[O:38])[C:34]([CH3:35])([CH3:36])[CH3:37])[C@H:23]3[O:24][C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27])=[N:5][N:4]([CH2:3][CH2:2][OH:1])[C:8]=2[CH:9]([CH3:11])[CH3:10])=[C:14]([CH3:20])[CH:15]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 80061-Bromo-3-chloropropaneHCID 14798Sodium HydroxideHCID 68943822HCID 68943822, compound

Product 1

HCID 68944549HCID 68944549, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1-(2-hydroxyethyl)-4-[(4-hydroxy-2-methylphenyl)methyl]-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.69 g), 1-bromo-3-chloropropane (0.22 mL) and tetra(n-butyl)ammonium bromide (0.14 g) in tetrahydrofuran (8 mL) was added 5 mol/L aqueous sodium hydroxide solution (0.43 mL), and the mixture was stirred at room temperature overnight. The reaction mixture was poured into 0.5 mol/L hydrochloric acid, and the resulting mixture was extracted with diethylether. The extract was washed with water and brine successively, and dried over anhydrous magnesium 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) to give the title compound (0.56 g).

Workup

  1. extractionthe resulting mixture was extracted with diethylether
  2. washThe extract was washed with water and brine successively
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by column chromatography on silica gel (eluent: n-hexane/ethyl acetate=1/1)

Sources & evidence

ORD record
ord-ffe2885c2e8246a394ca662040bfc7ab
Source dataset
uspto-grants-2012_12
Patent number
US08324176B2

Reaction notes

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