Ammonium Chloride → 3-(beta-D-Glucopyranosyloxy)-5-isopropyl-4-[(4-{(1E)-2-[2-(sulfamoylamino)ethylcarbamoyl]vinyl}-2-methylphenyl)-methyl]-1H-pyrazole

HRID 2223610Notes

Reaction equation

HRID 2223610 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](/[CH:37]=[CH:38]/[C:39](O)=[O:40])=[CH:33][C:32]=2[CH3:42])=[C:28]([CH:43]([CH3:45])[CH3:44])[NH:27][N:26]=1)(=O)C.[S:46]([NH:50][CH2:51][CH2:52][NH2:53])(=[O:49])(=[O:48])[NH2:47].[Cl-].[NH4+]>>[C@@H:6]1([O:24][C:25]2[C:29]([CH2:30][C:31]3[CH:36]=[CH:35][C:34](/[CH:37]=[CH:38]/[C:39](=[O:40])[NH:53][CH2:52][CH2:51][NH:50][S:46](=[O:49])(=[O:48])[NH2:47])=[CH:33][C:32]=3[CH3:42])=[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 25517Ammonium ChlorideHCID 23077839[(2-Aminoethyl)sulfamoyl]amineHCID 685378523-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-4-({4-[(1E)-2-carboxyvinyl]-2-methylphenyl}methyl)-5-isopropyl-1H-pyrazole

Product 1

HCID 685376623-(beta-D-Glucopyranosyloxy)-5-isopropyl-4-[(4-{(1E)-2-[2-(sulfamoylamino)ethylcarbamoyl]vinyl}-2-methylphenyl)-methyl]-1H-pyrazole

Procedure

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

Sources & evidence

ORD record
ord-ec182a248eff48408538c7242af601fd
Source dataset
uspto-grants-2008_05
Patent number
US07375087B2

Reaction notes

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