4-Methoxybenzyl bromide → methyl (S)-2-(4-methanesulphonylpiperazin-1-yl)-3-[4-(4-methoxybenzyloxy)benzoylamino]propanoate

HRID 517514Notes

Reaction equation

HRID 517514 reaction equation
[OH:1][C:2]1[CH:26]=[CH:25][C:5]([C:6]([NH:8][CH2:9][C@H:10]([N:15]2[CH2:20][CH2:19][N:18]([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:17][CH2:16]2)[C:11]([O:13][CH3:14])=[O:12])=[O:7])=[CH:4][CH:3]=1.Br[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=1>>[CH3:24][S:21]([N:18]1[CH2:17][CH2:16][N:15]([C@@H:10]([CH2:9][NH:8][C:6](=[O:7])[C:5]2[CH:25]=[CH:26][C:2]([O:1][CH2:28][C:29]3[CH:34]=[CH:33][C:32]([O:35][CH3:36])=[CH:31][CH:30]=3)=[CH:3][CH:4]=2)[C:11]([O:13][CH3:14])=[O:12])[CH2:20][CH2:19]1)(=[O:23])=[O:22]

Participants

3

Reactant 2

HCID 1650214-Methoxybenzyl bromideHCID 67056914methyl (S)-3-(4-hydroxybenzoylamino)-2-(4-methanesulphonylpiperazin-1-yl)propanoate

Product 1

HCID 67057035methyl (S)-2-(4-methanesulphonylpiperazin-1-yl)-3-[4-(4-methoxybenzyloxy)benzoylamino]propanoateYield 100%

Procedure

In a manner similar to example 4-5, starting from 300 mg (0.8 mmol) of methyl (S)-3-(4-hydroxybenzoylamino)-2-(4-methanesulphonylpiperazin-1-yl)propanoate (prepared as described in example 4-4) and from 0.14 ml (0.9 mmol) of 1-bromomethyl-4-methoxybenzene; 390 mg (100%) of methyl (S)-2-(4-methanesulphonylpiperazin-1-yl)-3-[4-(4-methoxybenzyloxy)benzoylamino]propanoate are obtained in the form of a colourless oil.

Sources & evidence

ORD record
ord-47170daad6ad4f28b9bb28bba460ea3d
Source dataset
uspto-grants-2015_08
Patent number
US09115102B2

Reaction notes

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