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

HRID 2223588Notes

Reaction equation

HRID 2223588 reaction equation
[NH2:1][C:2]([CH3:7])([CH2:5][OH:6])[CH2:3][OH:4].C([O:11][C@@H:12]1[C@@H:17]([O:18]C(=O)C)[C@H:16]([O:22]C(=O)C)[C@@H:15]([CH2:26][O:27]C(=O)C)[O:14][C@H:13]1[O:31][C:32]1[C:36]([CH2:37][C:38]2[CH:43]=[CH:42][C:41](/[CH:44]=[CH:45]/[C:46](O)=[O:47])=[CH:40][CH:39]=2)=[C:35]([CH:49]([CH3:51])[CH3:50])[NH:34][N:33]=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:13]1([O:31][C:32]2[C:36]([CH2:37][C:38]3[CH:43]=[CH:42][C:41](/[CH:44]=[CH:45]/[C:46](=[O:47])[NH:1][C:2]([CH2:5][OH:6])([CH3:7])[CH2:3][OH:4])=[CH:40][CH:39]=3)=[C:35]([CH:49]([CH3:51])[CH3:50])[NH:34][N:33]=2)[O:14][C@H:15]([CH2:26][OH:27])[C@@H:16]([OH:22])[C@H:17]([OH:18])[C@H:12]1[OH:11]

Participants

4

Reactant 3

HCID 15312-Amino-2-methyl-1,3-propanediolHCID 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 685429633-(beta-D-Glucopyranosyloxy)-4-[(4-{(1E)-2-[2-hydroxy-1-hydroxymethyl-1-(methyl)-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 2-amino-2-methyl-1,3-propanediol and 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-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-5adc8241c8ea42fa8c3d8932c9fefe26
Source dataset
uspto-grants-2008_05
Patent number
US07375087B2

Reaction notes

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