Methyl bromoacetate → HCID 16727481, compound

HRID 1007733Notes

Reaction equation

HRID 1007733 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 16727481HCID 16727481, compound

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-ee06f3081b804b0795c041cd178c20e1
Source dataset
uspto-grants-2004_09
Patent number
US06794404B2

Reaction notes

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