Water → HCID 11178653, compound

HRID 1673321Notes

Reaction equation

HRID 1673321 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[C:8]([CH2:13][CH2:14][C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)[CH:9]=[CH:10][CH:11]=2)[C:6]([O:22][C@@H:23]2[O:49][C@H:48]([CH2:50][O:51]C(=O)C(C)(C)C)[C@@H:40]([O:41]C(=O)C(C)(C)C)[C@H:32]([O:33]C(=O)C(C)(C)C)[C@H:24]2[O:25]C(=O)C(C)(C)C)=[N:5]1.O.O.[OH-].[Li+]>CO>[C@@H:23]1([O:22][C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][C:8]=3[CH2:13][CH2:14][C:15]3[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=3)[N:4]([CH2:3][CH2:2][OH:1])[N:5]=2)[O:49][C@H:48]([CH2:50][OH:51])[C@@H:40]([OH:41])[C@H:32]([OH:33])[C@H:24]1[OH:25]

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 67341380HCID 67341380, compound

Product 1

HCID 11178653HCID 11178653, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 1-(2-hydroxyethyl)-4-[2-(4-hydroxy-phenyl)ethyl]-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-indazole (0.31 g) in methanol (6 mL) were added water (0.6 mL) and lithium hydroxide monohydrate (0.16 g), and the mixture was stirred at room temperature for 8 hours. The reaction mixture was concentrated under reduced pressure, and the residue was dissolved in water. To the solution was added acetic acid (0.45 mL), and the resulting mixture was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol) to give the title compound (0.14 g)

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe residue was dissolved in water
  3. additionTo the solution was added acetic acid (0.45 mL)
  4. distillationthe resulting mixture was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol)

Sources & evidence

ORD record
ord-3825ffa15c664bcd9c14e89a4584c997
Source dataset
uspto-grants-2011_08
Patent number
US07998975B2

Reaction notes

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