Sodium Methoxide → HCID 68945442, compound

HRID 1868972Notes

Reaction equation

HRID 1868972 reaction equation
C([O:4][C@@H:5]1[C@@H:10]([O:11]C(=O)C)[C@H:9]([O:15]C(=O)C)[C@@H:8]([CH2:19][O:20]C(=O)C)[O:7][C@H:6]1[O:24][C:25]1[C:29]([CH2:30][C:31]2[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][CH2:40][NH2:41])=[CH:33][CH:32]=2)=[C:28]([CH:42]([CH3:44])[CH3:43])[NH:27][N:26]=1)(=O)C.C[O-].[Na+]>CO>[NH2:41][CH2:40][CH2:39][CH2:38][O:37][C:34]1[CH:33]=[CH:32][C:31]([CH2:30][C:29]2[C:25]([O:24][C@@H:6]3[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]3[OH:4])=[N:26][NH:27][C:28]=2[CH:42]([CH3:44])[CH3:43])=[CH:36][CH:35]=1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 68937787HCID 68937787, compound

Product 1

HCID 68945442HCID 68945442, compoundYield 78.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-{[4-(3-aminopropoxy)phenyl]methyl}-5-isopropyl-1H-pyrazole (0.1 g) in methanol (2 mL) was added sodium methoxide (28% methanol solution, 0.062 mL), and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated under reduced pressure, and the residue was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol) to give the title compound (57 mg).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. distillationthe residue was purified by solid phase extraction on ODS (washing solvent: distilled water, eluent: methanol)

Sources & evidence

ORD record
ord-5c5b80cbf469496fab03ace264d3d620
Source dataset
uspto-grants-2009_12
Patent number
US07635684B2

Reaction notes

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