Methyl bromoacetate → HCID 490786, compound

HRID 1007718Notes

Reaction equation

HRID 1007718 reaction equation
Cl.C[O:3][C:4](=[O:17])[C@H:5]([CH2:7][C:8]1[CH:13]=[C:12]([F:14])[C:11]([OH:15])=[C:10]([F:16])[CH:9]=1)[NH2:6].[CH:18]1([N:24]2[C:28]3[CH:29]=[CH:30][C:31](C(O)=O)=[CH:32][C:27]=3[N:26]=[C:25]2[C:36]2[CH:40]=[CH:39][O:38][CH:37]=2)[CH2:23][CH2:22][CH2:21][CH2:20][CH2:19]1.Br[CH2:42][C:43]([O:45]C)=[O:44].[C:47]([O-])([O-])=[O:48].[K+].[K+].CC(C)=O>>[C:43]([CH2:42][O:15][C:11]1[C:12]([F:14])=[CH:13][C:8]([CH2:7][CH:5]([NH:6][C:47]([C:31]2[CH:30]=[CH:29][C:28]3[N:24]([CH:18]4[CH2:19][CH2:20][CH2:21][CH2:22][CH2:23]4)[C:25]([C:36]4[CH:40]=[CH:39][O:38][CH:37]=4)=[N:26][C:27]=3[CH:32]=2)=[O:48])[C:4]([OH:3])=[O:17])=[CH:9][C:10]=1[F:16])([OH:45])=[O:44]

Participants

5

Reactant 4

HCID 60984Methyl bromoacetateHCID 4911131-Cyclohexyl-2-(furan-3-yl)-1H-benzimidazole-5-carboxylic acidHCID 69315745Racemic 3,5-difluorotyrosine methyl ester hydrochlorideHCID 86600397Acetone potassium carbonate

Product 1

HCID 490786HCID 490786, compound

Procedure

Racemic 3,5-difluorotyrosine 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 ester groups saponified to give the title compound of example 125.

Sources & evidence

ORD record
ord-47d9042eec104983bf0cca8548074cbf
Source dataset
uspto-grants-2004_09
Patent number
US06794404B2

Reaction notes

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