Sodium Methoxide → HCID 67341909, compound

HRID 2223965Notes

Reaction equation

[OH:1][CH2:2][CH2:3][CH2:4][N:5]1[C:9]2=[N:10][CH:11]=[CH:12][C:13]([CH2:14][CH2:15][C:16]3[CH:21]=[CH:20][C:19]([O:22]C(=O)C(C)(C)C)=[CH:18][CH:17]=3)=[C:8]2[C:7]([O:29][C@@H:30]2[O:38][C@H:37]([CH:39](C(=O)C(C)(C)C)[OH:40])[C@@:35](C(=O)C(C)(C)C)([OH:36])[C@:33](C(=O)C(C)(C)C)([OH:34])[C@@:31]2(C(=O)C(C)(C)C)[OH:32])=[N:6]1.C[O-].[Na+]>CO>[C@@H:30]1([O:29][C:7]2[C:8]3[C:9](=[N:10][CH:11]=[CH:12][C:13]=3[CH2:14][CH2:15][C:16]3[CH:17]=[CH:18][C:19]([OH:22])=[CH:20][CH:21]=3)[N:5]([CH2:4][CH2:3][CH2:2][OH:1])[N:6]=2)[O:38][C@H:37]([CH2:39][OH:40])[C@@H:35]([OH:36])[C@H:33]([OH:34])[C@H:31]1[OH:32]

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 1-(3-hydroxypropyl)-3-(2,3,4,6-tetra-pivaloyl-β-D-glucopyranosyloxy)-4-[2-(4-pivaloyloxy-phenyl) ethyl]-1H-pyrazolo [3, 4-b]pyridine (40 mg) in methanol (2 mL) was added sodium methoxide (28% methanol solution, 0.04 mL), and the mixture was stirred at 60° 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 (18 mg).

Workup

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

Sources & evidence

ORD record: ord-3ee4af8c56dc4c84beefff1581017c17
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07375113B2

Reaction notes

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