Sodium Methoxide → HCID 68941034, compound

HRID 1869030Notes

Reaction equation

HRID 1869030 reaction equation
[C:1]([CH2:4][CH2:5][NH:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]2[C:19]([O:30][C@@H:31]3[O:57][C@H:56]([CH2:58][O:59]C(=O)C(C)(C)C)[C@@H:48]([O:49]C(=O)C(C)(C)C)[C@H:40]([O:41]C(=O)C(C)(C)C)[C@H:32]3[O:33]C(=O)C(C)(C)C)=[N:20][N:21]([CH2:26][CH2:27][CH2:28][OH:29])[C:22]=2[CH:23]([CH3:25])[CH3:24])=[C:13]([CH3:66])[CH:12]=1)(=[O:3])[NH2:2].C[O-].[Na+]>CO>[C:1]([CH2:4][CH2:5][NH:6][CH2:7][CH2:8][CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][C:18]2[C:19]([O:30][C@@H:31]3[O:57][C@H:56]([CH2:58][OH:59])[C@@H:48]([OH:49])[C@H:40]([OH:41])[C@H:32]3[OH:33])=[N:20][N:21]([CH2:26][CH2:27][CH2:28][OH:29])[C:22]=2[CH:23]([CH3:25])[CH3:24])=[C:13]([CH3:66])[CH:12]=1)(=[O:3])[NH2:2]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 86602036HCID 86602036, compound

Product 1

HCID 68941034HCID 68941034, compoundYield 83.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 4-[(4-{3-[2-(carbamoyl)ethylamino]-propoxy}-2-methylphenyl)methyl]-1-(3-hydroxypropyl)-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazole (0.3 g) in methanol (6 mL) was added sodium methoxide (28% methanol solution, 0.25 mL), and the mixture was stirred at 50° C. overnight. 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 (0.16 g).

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-2f9130aafa4d465ea07ca0144b33835f
Source dataset
uspto-grants-2009_12
Patent number
US07635684B2

Reaction notes

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