[(2-Nitrophenylsulfonyl)amino]acetamide → 3-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-4-[(4-{3-[(S)-1-(carbamoyl)ethylamino]propoxy}phenyl)methyl]-5-isopropyl-1H-pyrazole

HRID 2189368Notes

Reaction equation

HRID 2189368 reaction equation
[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[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]CCCO)=[CH:33][CH:32]=2)=[C:28]([CH:42]([CH3:44])[CH3:43])[NH:27][N:26]=1)(=[O:3])[CH3:2].[N+](C1C=CC=CC=1S([NH:57][C@@H:58]([CH3:62])[C:59]([NH2:61])=[O:60])(=O)=O)([O-])=O.[N+]([C:66]1[CH:71]=CC=C[C:67]=1S(NCC(N)=O)(=O)=O)([O-])=O>>[C:1]([O:4][C@@H:5]1[C@@H:10]([O:11][C:12](=[O:14])[CH3:13])[C@H:9]([O:15][C:16](=[O:18])[CH3:17])[C@@H:8]([CH2:19][O:20][C:21](=[O:23])[CH3:22])[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][CH2:67][CH2:66][CH2:71][NH:57][C@H:58]([C:59](=[O:60])[NH2:61])[CH3:62])=[CH:33][CH:32]=2)=[C:28]([CH:42]([CH3:43])[CH3:44])[NH:27][N:26]=1)(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 23078895[(2-Nitrophenylsulfonyl)amino]acetamideHCID 689429023-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-4-{[4-(3-hydroxypropoxy)phenyl]methyl}-5-isopropyl-1H-pyrazoleHCID 68945906(S)-2-(2-nitrobenzenesulfonylamino)propionamide

Product 1

HCID 689425743-(2,3,4,6-Tetra-O-acetyl-beta-D-glucopyranosyloxy)-4-[(4-{3-[(S)-1-(carbamoyl)ethylamino]propoxy}phenyl)methyl]-5-isopropyl-1H-pyrazole

Procedure

The title compound was prepared in a similar manner to that described in Example 39 using 3-(2,3,4,6-tetra-O-acetyl-β-D-glucopyranosyloxy)-4-{[4-(3-hydroxypropoxy)phenyl]-methyl}-5-isopropyl-1H-pyrazole and (S)-2-(2-nitrobenzenesulfonylamino)propionamide 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-(2-nitrobenzenesulfonylamino)acetoamide, respectively.

Sources & evidence

ORD record
ord-f0b81ebbf0d749539c81be5e48592427
Source dataset
uspto-grants-2012_12
Patent number
US08324176B2

Reaction notes

Loading…