2-Amino-2-methylpropanamide → 4-[(4-{(1E)-2-[1-Carbamoyl-1-(methyl)-ethylcarbamoyl]vinyl}phenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole

HRID 1442374Notes

Reaction equation

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

Participants

Reactant 3

HCID 64537832-Amino-2-methylpropanamide

HCID 685375513-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-4-({4-[(1E)-3-carboxyprop-1-enyl]phenyl}methyl)-5-isopropyl-1H-pyrazole

HCID 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 685408084-[(4-{(1E)-2-[1-Carbamoyl-1-(methyl)-ethylcarbamoyl]vinyl}phenyl)methyl]-3-(beta-D-glucopyranosyloxy)-5-isopropyl-1H-pyrazole

Procedure

The title compound was prepared in a similar manner to that described in Example 26 using 2-amino-2-methylpropionamide 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-0747f927b98d459b8d65973943e787af
Source dataset: uspto-grants-2010_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07655632B2

Reaction notes

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