1,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride → 2,6-dinitro-4-[3',5'-bis(N-methylacetamido)-2',4',6'-triiodophenyl]-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine
Reaction equation
[I:1][C:2]1[C:7]([N:8]([CH3:12])[C:9](=[O:11])[CH3:10])=[C:6]([I:13])[C:5]([N:14]([CH3:18])[C:15](=[O:17])[CH3:16])=[C:4]([I:19])[C:3]=1[C:20]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[C:23]([C:29](O)=[O:30])=[C:22]([N+:32]([O-:34])=[O:33])[CH:21]=1.[C:35]([O:38][CH:39]1[O:53][C@H:52]([CH2:54][O:55][C:56](=[O:58])[CH3:57])[C@@H:47]([O:48][C:49](=[O:51])[CH3:50])[C@H:42]([O:43][C:44](=[O:46])[CH3:45])[C@H:40]1[NH2:41])(=[O:37])[CH3:36].Cl.CN(C)CCCN=C=NCC>>[N+:32]([C:22]1[CH:21]=[C:20]([C:3]2[C:4]([I:19])=[C:5]([N:14]([CH3:18])[C:15](=[O:17])[CH3:16])[C:6]([I:13])=[C:7]([N:8]([CH3:12])[C:9](=[O:11])[CH3:10])[C:2]=2[I:1])[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[C:23]=1[C:29]([C:39]1([O:53][C@H:52]([CH2:54][O:55][C:56](=[O:58])[CH3:57])[C@@H:47]([O:48][C:49](=[O:51])[CH3:50])[C@H:42]([O:43][C:44](=[O:46])[CH3:45])[C@H:40]1[NH2:41])[O:38][C:35](=[O:37])[CH3:36])=[O:30])([O-:34])=[O:33]Participants
4
Reactant 3
Product 1
Procedure
2′,4′,6′-triiodo-3′,5′-bis(N-methylacetamido)-3,5-dinitrobiphenyl-4-carboxylic acid (14) 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 2,6-dinitro-4-[3′,5′-bis(N-methylacetamido)-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 treatment with sodium carbonate in methanol to yield 2,6-dinitro-4-[3′,5′-bis(N-methylacetamido)-2′,4′,6′-triiodophenyl]-benzoyl-D-glucosamine (15).
Sources & evidence
- ORD record
- ord-62890178de41453d8842c772ee4a1a55
- Source dataset
- uspto-grants-2004_04
- Patent number
- US06723746B2
Reaction notes
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