alpha-Acetobromogalactose → HCID 13271634, compound

HRID 358146Notes

Reaction equation

[C:1]([C:4]1[N+:8]([CH2:9][C:10]2[CH:15]=[CH:14][C:13]([N+:16]([O-:18])=[O:17])=[CH:12][CH:11]=2)=[CH:7][NH:6][C:5]=1[O-:19])(=[O:3])[NH2:2].[C:20]([O:23][C@@H:24]1[C@@H:29]([O:30][C:31](=[O:33])[CH3:32])[C@@H:28]([O:34][C:35](=[O:37])[CH3:36])[C@@H:27]([CH2:38][O:39][C:40](=[O:42])[CH3:41])[O:26][C@@H:25]1Br)(=[O:22])[CH3:21]>>[N+:16]([C:13]1[CH:12]=[CH:11][C:10]([CH2:9][N:8]2[C:4]([C:1]([NH2:2])=[O:3])=[C:5]([O:19][C@@H:25]3[O:26][C@H:27]([CH2:38][O:39][C:40](=[O:42])[CH3:41])[C@H:28]([O:34][C:35](=[O:37])[CH3:36])[C@H:29]([O:30][C:31](=[O:33])[CH3:32])[C@H:24]3[O:23][C:20](=[O:22])[CH3:21])[N:6]=[CH:7]2)=[CH:15][CH:14]=1)([O-:18])=[O:17]

Participants

Reactant 2

HCID 2734143alpha-Acetobromogalactose

HCID 178513772HCID 178513772, compound

Product 1

HCID 13271634HCID 13271634, compoundYield 65.1%

Procedure

Following a procedure similar to that of Example 1 but using 2.622 g of 5-carbamoyl-1-(4-nitrobenzyl)imidazolium-4-olate and 8.220 g of 2,3,4,6-tetra-O-acetyl-α-D-galactopyranosyl bromide there was obtained 3.857 g of 1-(4-nitrobenzyl)-4-(2,3,4,6-tetra-O-acetyl-β-D-galactopyranosyl)oxy-1H-imidazole-5-carboxamide.

Sources & evidence

ORD record: ord-ce92fcd38df049dfbebb3a6664ab2c22
Source dataset: uspto-grants-1984_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04464531

Reaction notes

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