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

HRID 1442373Notes

Reaction equation

HRID 1442373 reaction equation
[OH:1][CH2:2][C:3]([CH2:7][OH:8])([CH2:5][OH:6])[NH2:4].C([O:12][C@@H:13]1[C@@H:18]([O:19]C(=O)C)[C@H:17]([O:23]C(=O)C)[C@@H:16]([CH2:27][O:28]C(=O)C)[O:15][C@H:14]1[O:32][C:33]1[C:37]([CH2:38][C:39]2[CH:44]=[CH:43][C:42](/[CH:45]=[CH:46]/[C:47](O)=[O:48])=[CH:41][CH:40]=2)=[C:36]([CH:50]([CH3:52])[CH3:51])[NH:35][N:34]=1)(=O)C.C(O[C@@H]1[C@@H](OC(=O)C)[C@H](OC(=O)C)[C@@H](COC(=O)C)O[C@H]1OC1C(CC2C=CC(/C=C/CC(O)=O)=CC=2)=C(C(C)C)NN=1)(=O)C>>[C@@H:14]1([O:32][C:33]2[C:37]([CH2:38][C:39]3[CH:44]=[CH:43][C:42](/[CH:45]=[CH:46]/[C:47](=[O:48])[NH:4][C:3]([CH2:7][OH:8])([CH2:5][OH:6])[CH2:2][OH:1])=[CH:41][CH:40]=3)=[C:36]([CH:50]([CH3:52])[CH3:51])[NH:35][N:34]=2)[O:15][C@H:16]([CH2:27][OH:28])[C@@H:17]([OH:23])[C@H:18]([OH:19])[C@H:13]1[OH:12]

Participants

4

Reactant 3

HCID 6503Tris(hydroxymethyl)aminomethaneHCID 685375513-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-4-({4-[(1E)-3-carboxyprop-1-enyl]phenyl}methyl)-5-isopropyl-1H-pyrazoleHCID 685386823-(2,3,4,6-tetra-O-acetyl-beta-D-gluco-pyranosyloxy)-4-({4-[(1E)-2-carboxyvinyl]phenyl}methyl)-5-isopropyl-1H-pyrazole

Product 1

HCID 685383263-(beta-D-Glucopyranosyloxy)-4-[(4-{(1E)-2-[2-hydroxy-1,1-bis-(hydroxymethyl)ethylcarbamoyl]vinyl}phenyl)methyl]-5-isopropyl-1H-pyrazole

Procedure

The title compound was prepared in a similar manner to that described in Example 26 using tris(hydroxymethyl)-aminomethane and 3-(2,3,4,6-tetra-O-acetyl-β-D-gluco-pyranosyloxy)-4-({4-[(1E)-2-carboxyvinyl]phenyl}methyl)-5-isopropyl-1H-pyrazole instead of ammonium chloride and 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-({4-[(1E)-3-carboxyprop-1-enyl]phenyl}methyl)-5-isopropyl-1H-pyrazole, respectively.

Sources & evidence

ORD record
ord-834b24cfdf0344f8b73a3e8eff9db57c
Source dataset
uspto-grants-2010_02
Patent number
US07655632B2

Reaction notes

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