Hydrochloric Acid → HCID 68944549, compound

HRID 1869024Notes

Reaction equation

HRID 1869024 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-dad8a705d7044f99bcb0cb3fdc324fc6
Source dataset
uspto-grants-2009_12
Patent number
US07635684B2

Reaction notes

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