2,6-Dimethoxy-3-(hydroxymethyl)benzeneboronic acid → N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-3-(hydroxymethyl)phenyl]-L-phenylalanine ethyl ester

HRID 24689Notes

Reaction equation

HRID 24689 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH2:9][OH:10])=[CH:7][CH:6]=[C:5]([O:11][CH3:12])[C:4]=1B(O)O.[CH2:16]([O:18][C:19](=[O:40])[C@H:20]([CH2:32][C:33]1[CH:38]=[CH:37][C:36](Br)=[CH:35][CH:34]=1)[NH:21][C:22](=[O:31])[C:23]1[C:28]([Cl:29])=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:30])[CH3:17]>>[CH2:16]([O:18][C:19](=[O:40])[C@H:20]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([C:4]2[C:5]([O:11][CH3:12])=[CH:6][CH:7]=[C:8]([CH2:9][OH:10])[C:3]=2[O:2][CH3:1])=[CH:35][CH:34]=1)[NH:21][C:22](=[O:31])[C:23]1[C:24]([Cl:30])=[CH:25][CH:26]=[CH:27][C:28]=1[Cl:29])[CH3:17]

Participants

3

Reactant 2

HCID 225718182,6-Dimethoxy-3-(hydroxymethyl)benzeneboronic acidHCID 54106344(S)-Ethyl 3-(4-bromophenyl)-2-(2,6-dichlorobenzamido)propanoate

Product 1

HCID 54057631N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-3-(hydroxymethyl)phenyl]-L-phenylalanine ethyl ester

Procedure

2,6-Dimethoxy-3-(hydroxymethyl)benzeneboronic acid was coupled with N-(2,6-dichlorobenzoyl)-4-bromo-L-phenylalanine ethyl ester in a similar method as described in Example 7-2) to give N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-3-(hydroxymethyl)phenyl]-L-phenylalanine ethyl ester.

Sources & evidence

ORD record
ord-7d54cf8a348c43769d85ac6070dedf22
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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