1-Cyclohexyl-2-(furan-3-yl)-1H-benzimidazole-5-carboxylic acid → (2S)-3-(3-azido-4-hydroxy-phenyl)-2-[[1-cyclohexyl-2-(3-furyl)benzimidazole-5-carbonyl]amino]propanoic acid
Reaction equation
[NH2:1][C@@H:2]([CH2:6][C:7]1[CH:12]=[CH:11][C:10]([OH:13])=[C:9]([N:14]=[N+:15]=[N-:16])[CH:8]=1)[C:3]([OH:5])=[O:4].[CH:17]1([N:23]2[C:27]3[CH:28]=[CH:29][C:30]([C:32](O)=[O:33])=[CH:31][C:26]=3[N:25]=[C:24]2[C:35]2[CH:39]=[CH:38][O:37][CH:36]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>>[N:14]([C:9]1[CH:8]=[C:7]([CH2:6][C@H:2]([NH:1][C:32]([C:30]2[CH:29]=[CH:28][C:27]3[N:23]([CH:17]4[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]4)[C:24]([C:35]4[CH:39]=[CH:38][O:37][CH:36]=4)=[N:25][C:26]=3[CH:31]=2)=[O:33])[C:3]([OH:5])=[O:4])[CH:12]=[CH:11][C:10]=1[OH:13])=[N+:15]=[N-:16]Participants
3
Procedure
To a solution of 3-amino-L-tyrosine.2HCl.H2O (2.50 g, 8.8 mmol) in 0.5 N HCl (28 mL) at 0° C., an aqueous solution of NaNO2 (0.724 g, 10.5 mmol, in 10 mL H2O) was added slowly. The reaction mixture was stirred for 10 min at 0° C., in the dark, and then a solution of NaN3 (1.43 g, 21.9 mmol, in 10 mL H2O) was added and stirring was continued for 1 h at 0° C. The white solid formed was filtered and dried to give (S)-2-amino-3-(3-azido-4-hydroxy-phenyl)-propionic acid (1.16 g) as of a beige solid. This amino acid was coupled to the carboxylic acid of example 2 in the usual manner to give the title compound of example 146 after purification by preparative C18 reversed-phase HPLC.
Sources & evidence
- ORD record
- ord-909329c689894f69ac9dc61ece356afc
- Source dataset
- uspto-grants-2002_11
- Patent number
- US06479508B1
Reaction notes
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