Sodium Iodide → 4-({4-[3-(Benzyloxycarbonyl)propoxy]-2-methylphenyl}-methyl)-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-pyrazole

HRID 1442412Notes

Reaction equation

HRID 1442412 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[C:10]([O:17][C@@H:18]3[O:44][C@H:43]([CH2:45][O:46][C:47](=[O:52])[C:48]([CH3:51])([CH3:50])[CH3:49])[C@@H:35]([O:36][C:37](=[O:42])[C:38]([CH3:41])([CH3:40])[CH3:39])[C@H:27]([O:28][C:29](=[O:34])[C:30]([CH3:33])([CH3:32])[CH3:31])[C@H:19]3[O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:24])[CH3:23])=[N:11][NH:12][C:13]=2[CH:14]([CH3:16])[CH3:15])=[C:4]([CH3:53])[CH:3]=1.Br[CH2:55][CH2:56][CH2:57][C:58]([O:60][CH2:61][C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1)=[O:59].C(=O)([O-])[O-].[Cs+].[Cs+].[I-].[Na+]>CN(C)C=O.O>[CH2:61]([O:60][C:58]([CH2:57][CH2:56][CH2:55][O:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]2[C:10]([O:17][C@@H:18]3[O:44][C@H:43]([CH2:45][O:46][C:47](=[O:52])[C:48]([CH3:51])([CH3:50])[CH3:49])[C@@H:35]([O:36][C:37](=[O:42])[C:38]([CH3:39])([CH3:41])[CH3:40])[C@H:27]([O:28][C:29](=[O:34])[C:30]([CH3:31])([CH3:32])[CH3:33])[C@H:19]3[O:20][C:21](=[O:26])[C:22]([CH3:25])([CH3:23])[CH3:24])=[N:11][NH:12][C:13]=2[CH:14]([CH3:16])[CH3:15])=[C:4]([CH3:53])[CH:3]=1)=[O:59])[C:62]1[CH:67]=[CH:66][CH:65]=[CH:64][CH:63]=1

Participants

7

Reactant 4

HCID 5238Sodium IodideHCID 10796Cesium carbonateHCID 3832489Benzyl 4-bromobutanoateHCID 685373584-[(4-Hydroxy-2-methylphenyl)methyl]-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-pyrazole

Product 1

HCID 866068504-({4-[3-(Benzyloxycarbonyl)propoxy]-2-methylphenyl}-methyl)-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-beta-D-glucopyranosyloxy)-1H-pyrazoleYield 64.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-[(4-hydroxy-2-methylphenyl)methyl]-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyl-oxy)-1H-pyrazole (0.2 g) in N,N-dimethylformamide (3 mL) were added benzyl 4-bromobutyrate (0.1 g), cesium carbonate (0.18 g) and a catalytic amount of sodium iodide, and the mixture was stirred at room temperature overnight. The reaction mixture was poured into water, and the resulting mixture was extracted with ethylacetate. The extract was washed with water and brine, 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=3/1-2/1) to give the title compound (0.16 g).

Workup

  1. extractionthe resulting mixture was extracted with ethylacetate
  2. washThe extract was washed with water and brine
  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=3/1-2/1)

Sources & evidence

ORD record
ord-463f2970aff5465981107304d7d6def8
Source dataset
uspto-grants-2010_02
Patent number
US07655632B2

Reaction notes

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