Methyl bromoacetate → Tyrosine, 3-carboxy-O-(carboxymethyl)-N-[[1-cyclohexyl-2-(3-furanyl)-1H-benzimidazol-5-yl]carbonyl]-

HRID 1018279Notes

Reaction equation

HRID 1018279 reaction equation
Cl.C[O:3][C:4](=[O:19])[C@H:5]([CH2:7][C:8]1[CH:13]=[CH:12][C:11]([OH:14])=[C:10]([C:15]([O:17]C)=[O:16])[CH:9]=1)[NH2:6].[CH:20]1([N:26]2[C:30]3[CH:31]=[CH:32][C:33]([C:35](O)=[O:36])=[CH:34][C:29]=3[N:28]=[C:27]2[C:38]2[CH:42]=[CH:41][O:40][CH:39]=2)[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]1.Br[CH2:44][C:45]([O:47]C)=[O:46].C([O-])([O-])=O.[K+].[K+].CC(C)=O>>[C:4]([CH:5]([NH:6][C:35]([C:33]1[CH:32]=[CH:31][C:30]2[N:26]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][CH2:21]3)[C:27]([C:38]3[CH:42]=[CH:41][O:40][CH:39]=3)=[N:28][C:29]=2[CH:34]=1)=[O:36])[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([O:14][CH2:44][C:45]([OH:47])=[O:46])=[C:10]([CH:9]=1)[C:15]([OH:17])=[O:16])([OH:3])=[O:19]

Participants

5

Reactant 4

HCID 60984Methyl bromoacetateHCID 4911131-Cyclohexyl-2-(furan-3-yl)-1H-benzimidazole-5-carboxylic acidHCID 69320169HCID 69320169, compoundHCID 86600397Acetone potassium carbonate

Product 1

HCID 491260Tyrosine, 3-carboxy-O-(carboxymethyl)-N-[[1-cyclohexyl-2-(3-furanyl)-1H-benzimidazol-5-yl]carbonyl]-

Procedure

Racemic 3-(carbomethoxy)tyrosine methyl ester hydrochloride (example 119) was coupled to the carboxylic acid of example 2 in the usual manner. The phenolic hydroxyl group was alkylated with methyl bromoacetate in the usual manner (K2CO3/acetone at reflux) and saponified to give the title compound of example 126.

Sources & evidence

ORD record
ord-2814fc92d8f54e6c81218265de2d0a3a
Source dataset
uspto-grants-2002_11
Patent number
US06479508B1

Reaction notes

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