Hydrochloric Acid → 2-Amino-4-(3'-ethyl-2',4',6'-triiodophenyl)-benzoyl-d-glucosamine
Reaction equation
[N+:1]([C:4]1[CH:35]=[C:34]([C:36]2[C:41]([I:42])=[CH:40][C:39]([I:43])=[C:38]([CH2:44][CH3:45])[C:37]=2[I:46])[CH:33]=[CH:32][C:5]=1[C:6]([C:8]1([O:26][C@H:25]([CH2:27][O:28]C(=O)C)[C@@H:20]([O:21]C(=O)C)[C@H:15]([O:16]C(=O)C)[C@H:13]1[NH2:14])[O:9]C(=O)C)=[O:7])([O-])=O.Cl>>[NH2:1][C:4]1[CH:35]=[C:34]([C:36]2[C:41]([I:42])=[CH:40][C:39]([I:43])=[C:38]([CH2:44][CH3:45])[C:37]=2[I:46])[CH:33]=[CH:32][C:5]=1[C:6]([C:8]1([O:26][C@H:25]([CH2:27][OH:28])[C@@H:20]([OH:21])[C@H:15]([OH:16])[C@H:13]1[NH2:14])[OH:9])=[O:7]Participants
Procedure
Freidel-Crafts acylation is performed on 2′,4′,6′-triiodo-3-nitrobiphenyl-4-carboxylic acid (6) in the presence of AlCl3 and CH3COCl to yield 2′,4′,6′-triiodo-3′-acetyl-3-nitrobiphenyl-4-carboxylic acid (12). C 13 H 6 I 3 N O 4 → C H 3 C O Cl Al Cl 3 C 15 H 8 I 3 N O 5 2′,4′,6′-triiodo-3′-acetyl-3-nitrobiphenyl-4-carboxylic acid (12) is then reacted with a zinc mercury amalgam and hydrochloric acid and heated to yield 2′,4′,6′-triiodo-3′-ethyl-3-nitrobiphenyl-4-carboxylic acid (13). C 15 H 8 I 3 N O 5 → Δ Zn ( Hg ) , H Cl C 15 H 10 I 3 N O 4 2′,4′,6′-triiodo-3′-ethyl-3-nitrobiphenyl-4-carboxylic acid (13) is reacted with thionyl chloride to yield 2′,4′,6′-triiodo-3′-ethyl-3-nitrobiphenyl-4-carbonyl chloride (14). C 15 H 10 I 3 N O 4 → S O Cl 2 C 15 H 9 Cl I 3 N O 3 1,3,4,6-tetra-O-acetyl-D-glucosamine (9) is reacted with 2′,4′,6′-triiodo-3′-ethyl-3-nitrobiphenyl-4-carbonyl chloride (14) to yield 2-nitro-4-(3′-ethyl-2′,4′,6′-triiodophenyl)-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (15). C14H21NO9+C15H9ClI3NO3→C29H29I3N2O12 2-nitro-4-(3′-ethyl-2′,4′,6′-triiodophenyl)-benzoyl-1,3,4,6-tetra-O-acetyl-D-glucosamine (15) is treated with stannous chloride and hydrochloric acid to yield 2-amino-4-(3′-ethyl-2′,4′,6′-triiodophenyl)-benzoyl-D-glucosamine (16). C 29 H 29 I 3 N 2 O 12 → Sn Cl 2 , H Cl C 21 H 23 I 3 N 2 O 6 Example 2 is similar in general structure to Example 1, with the additional presence of a short alkyl chain attached to the radio-opaque tri-iodophenyl moiety at the C-3′ position to further increase lipophilicity of the molecule and enhance cell membrane permeability. The computed logP of Example 2 is 5.31.
Sources & evidence
- ORD record
- ord-3148ca06fb094b389c509dc2d366203e
- Source dataset
- uspto-grants-2005_08
- Patent number
- US06923950B2
Reaction notes
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