Tris(hydroxymethyl)aminomethane → 3-(beta-D-Glucopyranosyloxy)-4-[(4-{3-[2-hydroxy-1,1-bis-(hydroxymethyl)ethylamino]propoxy}phenyl)methyl]-5-isopropyl-1H-pyrazole

HRID 2189380Notes

Reaction equation

HRID 2189380 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]O)=[CH:33][CH:32]=2)=[C:28]([CH:42]([CH3:44])[CH3:43])[NH:27][N:26]=1)(=O)C.[CH2:45]([OH:52])[C:46]([NH2:51])([CH2:49][OH:50])[CH2:47][OH:48].NC(C)(C)CO>>[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][CH2:40][NH:51][C:46]([CH2:49][OH:50])([CH2:47][OH:48])[CH2:45][OH:52])=[CH:33][CH:32]=3)=[C:28]([CH:42]([CH3:44])[CH3:43])[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 6503Tris(hydroxymethyl)aminomethaneHCID 118072-Amino-2-methyl-1-propanolHCID 689429023-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-4-{[4-(3-hydroxypropoxy)phenyl]methyl}-5-isopropyl-1H-pyrazole

Product 1

HCID 689453983-(beta-D-Glucopyranosyloxy)-4-[(4-{3-[2-hydroxy-1,1-bis-(hydroxymethyl)ethylamino]propoxy}phenyl)methyl]-5-isopropyl-1H-pyrazole

Procedure

The title compound was prepared in a similar manner to that described in Example 57 using 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-{[4-(3-hydroxypropoxy)phenyl]-methyl}-5-isopropyl-1H-pyrazole and tris(hydroxymethyl)aminomethane instead of 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-{[4-(3-hydroxypropoxy)-2-methylphenyl]methyl}-5-isopropyl-1H-pyrazole and 2-amino-2-methyl-1-propanol, respectively.

Sources & evidence

ORD record
ord-36bec375c141430e90132c5ff5eb85f6
Source dataset
uspto-grants-2012_12
Patent number
US08324176B2

Reaction notes

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