2-Amino-2-methyl-1-propanol → 3-(beta-D-Glucopyranosyloxy)-4-[(4-{2-[2-hydroxy-1,1-di-(methyl)ethylcarbamoyl]ethoxy}phenyl)methyl]-5-isopropyl-1H-pyrazole

HRID 2223641Notes

Reaction equation

HRID 2223641 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][C:40](O)=[O:41])=[CH:33][CH:32]=2)=[C:28]([CH:43]([CH3:45])[CH3:44])[NH:27][N:26]=1)(=O)C.[NH2:46][C:47]([CH3:51])([CH3:50])[CH2:48][OH:49].NC(C)(C)C(N)=O>>[C@@H:6]1([O:24][C:25]2[C:29]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([O:37][CH2:38][CH2:39][C:40](=[O:41])[NH:46][C:47]([CH3:51])([CH3:50])[CH2:48][OH:49])=[CH:33][CH:32]=3)=[C:28]([CH:43]([CH3:45])[CH3:44])[NH:27][N:26]=2)[O:7][C@H:8]([CH2:19][OH:20])[C@@H:9]([OH:15])[C@H:10]([OH:11])[C@H:5]1[OH:4]

Participants

4

Reactant 3

HCID 118072-Amino-2-methyl-1-propanolHCID 64537832-Amino-2-methylpropanamideHCID 685359803-(2,3,4,6-tetra-O-acetyl-beta-D-glucopyranosyloxy)-4-{[4-(2-carboxyethoxy)-phenyl]methyl}-5-isopropyl-1H-pyrazole

Product 1

HCID 685409063-(beta-D-Glucopyranosyloxy)-4-[(4-{2-[2-hydroxy-1,1-di-(methyl)ethylcarbamoyl]ethoxy}phenyl)methyl]-5-isopropyl-1H-pyrazole

Procedure

The title compound was prepared in a similar manner to that described in Example 78 using 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-{[4-(2-carboxyethoxy)phenyl]methyl}-5-isopropyl-1H-pyrazole and 2-amino-2-methyl-1-propanol instead of 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-{[4-(2-carboxyethoxy)-2-methylphenyl]methyl}-5-isopropyl-1H-pyrazole and 2-amino-2-methylpropionamide, respectively.

Sources & evidence

ORD record
ord-4894ac077b8846efab0be1ae55c9e55c
Source dataset
uspto-grants-2008_05
Patent number
US07375087B2

Reaction notes

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