Sodium Methoxide → 4-[(4-{3-[N-Benzyl-N-(2-carbamoylethyl)amino]-propoxy}-2-methylphenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole

HRID 1869031Notes

Reaction equation

[CH2:1]([N:8]([CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]2[C:26]([O:33][C@@H:34]3[O:60][C@H:59]([CH2:61][O:62]C(=O)C(C)(C)C)[C@@H:51]([O:52]C(=O)C(C)(C)C)[C@H:43]([O:44]C(=O)C(C)(C)C)[C@H:35]3[O:36]C(=O)C(C)(C)C)=[N:27][NH:28][C:29]=2[CH:30]([CH3:32])[CH3:31])=[C:20]([CH3:69])[CH:19]=1)[CH2:9][CH2:10][C:11](=[O:13])[NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[O-].[Na+]>CO>[CH2:1]([N:8]([CH2:14][CH2:15][CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25]2[C:26]([O:33][C@@H:34]3[O:60][C@H:59]([CH2:61][OH:62])[C@@H:51]([OH:52])[C@H:43]([OH:44])[C@H:35]3[OH:36])=[N:27][NH:28][C:29]=2[CH:30]([CH3:32])[CH3:31])=[C:20]([CH3:69])[CH:19]=1)[CH2:9][CH2:10][C:11](=[O:13])[NH2:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of 4-[(4-{3-[N-benzyl-N-(2-carbamoylethyl)amino]propoxy}-2-methylphenyl)methyl]-5-isopropyl-3-(2,3,4,6-tetra-O-pivaloyl-β-D-glucopyranosyloxy)-1H-pyrazole (1.25 g) in methanol (13 mL) was added sodium methoxide (28% methanol solution, 0.25 mL), and the mixture was stirred at 50° C. for 6 hours. The reaction mixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1-5/1) to give the title compound (0.5 g).

Workup

concentrationThe reaction mixture was concentrated under reduced pressure
customthe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1-5/1)

Sources & evidence

ORD record: ord-fc741f5a657a4e9fbed7a08dcb7e0bf5
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635684B2

Reaction notes

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