Water → 1-(benzyloxy-carbonyl)-3-(6-O-ethoxycarbonyl-beta-D-glucopyranosyloxy)-4-((4-isopropoxyphenyl)methyl]-5-methylpyrazole

HRID 33131Notes

Reaction equation

HRID 33131 reaction equation
[CH2:1]([O:8][C:9]([N:11]1[C:15]([CH3:16])=[C:14]([CH2:17][C:18]2[CH:23]=[CH:22][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[CH:20][CH:19]=2)[C:13]([O:28][C@@H:29]2[O:37][C@H:36]([CH2:38][OH:39])[C@@H:34]([OH:35])[C@H:32]([OH:33])[C@H:30]2[OH:31])=[N:12]1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[C:41]([O:43][CH2:44][CH3:45])=[O:42].O.O.C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CC1C=C(C)C=C(C)N=1>[CH2:1]([O:8][C:9]([N:11]1[C:15]([CH3:16])=[C:14]([CH2:17][C:18]2[CH:19]=[CH:20][C:21]([O:24][CH:25]([CH3:27])[CH3:26])=[CH:22][CH:23]=2)[C:13]([O:28][C@@H:29]2[O:37][C@H:36]([CH2:38][O:39][C:41]([O:43][CH2:44][CH3:45])=[O:42])[C@@H:34]([OH:35])[C@H:32]([OH:33])[C@H:30]2[OH:31])=[N:12]1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10928Ethyl chloroformateHCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 673349881-(benzyloxycarbonyl)-3-(beta-D-gluco-pyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-pyrazole

Product 1

HCID 235431641-(benzyloxy-carbonyl)-3-(6-O-ethoxycarbonyl-beta-D-glucopyranosyloxy)-4-((4-isopropoxyphenyl)methyl]-5-methylpyrazole

Reagents, catalysts & solvents 1

HCID 79532,4,6-TrimethylpyridineSolvent

Procedure

To a solution of 1-(benzyloxycarbonyl)-3-(β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methyl-pyrazole (0.20 g) in 2,4,6-trimethylpyridine (4 mL) was added ethyl chloroformate (0.092 mL), and the mixture was stirred at room temperature for 1 day. To the reaction mixture were added water and citric acid monohydrate, and the resulting mixture was extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1) to give 1-(benzyloxy-carbonyl)-3-(6-O-ethoxycarbonyl-β-D-glucopyranosyloxy)-4-[(4-isopropoxyphenyl)methyl]-5-methylpyrazole (0.17 g).

Workup

  1. extractionthe resulting mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with water
  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: dichloromethane/methanol=10/1)

Sources & evidence

ORD record
ord-7b6df4ceb90e4d3d8381a11c3aeb7cee
Source dataset
uspto-grants-2008_09
Patent number
US07429568B2

Reaction notes

Loading…