Methyl bromoacetate → (2S)-3-[5-(carboxymethyloxy)-1H-indol-3-yl]-2-[[1-cyclohexyl-2-(3-furyl)-6-methyl-benzimidazole-5-carbonyl]amino]propanoic acid

HRID 1280108Notes

Reaction equation

HRID 1280108 reaction equation
[CH:1]1([N:7]2[C:11]3[CH:12]=[C:13]([CH3:19])[C:14]([C:16](O)=[O:17])=[CH:15][C:10]=3[N:9]=[C:8]2[C:20]2[CH:24]=[CH:23][O:22][CH:21]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Cl.C[O:27][C:28](=[O:42])[C@H:29]([CH2:31][C:32]1[C:40]2[C:35](=[CH:36][CH:37]=[C:38]([OH:41])[CH:39]=2)[NH:34][CH:33]=1)[NH2:30].Br[CH2:44][C:45]([O:47]C)=[O:46]>>[C:45]([CH2:44][O:41][C:38]1[CH:39]=[C:40]2[C:35](=[CH:36][CH:37]=1)[NH:34][CH:33]=[C:32]2[CH2:31][C@H:29]([NH:30][C:16]([C:14]1[C:13]([CH3:19])=[CH:12][C:11]2[N:7]([CH:1]3[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]3)[C:8]([C:20]3[CH:24]=[CH:23][O:22][CH:21]=3)=[N:9][C:10]=2[CH:15]=1)=[O:17])[C:28]([OH:27])=[O:42])([OH:47])=[O:46]

Participants

4

Reactant 3

HCID 60984Methyl bromoacetateHCID 3012619HCID 3012619, compoundHCID 24802218methyl (2S)-2-amino-3-(5-hydroxy-1H-indol-3-yl)propanoate hydrochloride

Product 1

HCID 16727481(2S)-3-[5-(carboxymethyloxy)-1H-indol-3-yl]-2-[[1-cyclohexyl-2-(3-furyl)-6-methyl-benzimidazole-5-carbonyl]amino]propanoic acid

Procedure

1-Cyclohexyl-2-furan-3-yl-6-methyl-1H-benzimidazole-5-carboxylic acid was coupled to 5-hydroxy-(S)-tryptophan methyl ester hydrochloride in the usual manner (Example 154). The material was then alkylated with methyl bromoacetate as described previously to give after deprotection by saponification and preparative C18 reversed-phase HPLC, the title compound of example 155.

Workup

  1. customto give after deprotection by saponification

Sources & evidence

ORD record
ord-1d57d60a0a54416b8774b1e45f097a87
Source dataset
uspto-grants-2002_09
Patent number
US06448281B1

Reaction notes

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