1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2-nitro-4-[3',5'-bis(carboxy)-2',4',6'-triiodophenyl]-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine
Reaction equation
[I:1][C:2]1[C:7](CC(O)=O)=[C:6]([I:12])[C:5](CC(O)=O)=[C:4]([I:17])[C:3]=1[C:18]1[CH:23]=[CH:22][C:21]([C:24](O)=[O:25])=[C:20]([N+:27]([O-:29])=[O:28])[CH:19]=1.[C:30]([O:33][CH:34]1[O:48][C@H:47]([CH2:49][O:50][C:51](=[O:53])[CH3:52])[C@@H:42]([O:43][C:44](=[O:46])[CH3:45])[C@H:37]([O:38][C:39](=[O:41])[CH3:40])[C@H:35]1[NH2:36])(=[O:32])[CH3:31].Cl.CN(C)CCCN=C=NCC>>[N+:27]([C:20]1[CH:19]=[C:18]([C:3]2[C:2]([I:1])=[C:7]([C:30]([OH:33])=[O:32])[C:6]([I:12])=[C:5]([C:39]([OH:41])=[O:38])[C:4]=2[I:17])[CH:23]=[CH:22][C:21]=1[C:24]([C:34]1([O:48][C@H:47]([CH2:49][O:50][C:51](=[O:53])[CH3:52])[C@@H:42]([O:43][C:44](=[O:46])[CH3:45])[C@H:37]([O:38][C:39](=[O:41])[CH3:40])[C@H:35]1[NH2:36])[O:33][C:30](=[O:32])[CH3:31])=[O:25])([O-:29])=[O:28]Participants
4
Reactant 3
Product 1
Procedure
2′,4′,6′-triiodo-3′,5′-bis(carboxymethyl)-3-nitrobiphenyl-4-carboxylic acid (18) is coupled with 1,3,4,6-tetra-O-acetyl-D-glucosamine in the presence of 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide hydrochloride and N-hydrosuccinamide to yield 2-nitro-4-[3′,5′-bis(carboxy)-2′,4′,6′-triiodophenyl]-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine. The protecting acetyl groups on the glucosamine moiety are removed by reaction with sodium hydroxide in methanol to yield 2-nitro-4-[3′,5′-bis(carboxy)-2′,4′,6′-triiodophenyl]-benzoyl-D-glucosamine (19).
Sources & evidence
- ORD record
- ord-d6be39ebdeb541b0a67de013af2f3c9f
- Source dataset
- uspto-grants-2004_06
- Patent number
- US06751290B2
Reaction notes
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