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

HRID 24678Notes

Reaction equation

HRID 24678 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([CH2:9][CH2:10][OH:11])[CH:6]=[C:5]([O:12][CH3:13])[C:4]=1B(O)O.[CH2:17]([O:19][C:20](=[O:41])[C@H:21]([CH2:33][C:34]1[CH:39]=[CH:38][C:37](Br)=[CH:36][CH:35]=1)[NH:22][C:23](=[O:32])[C:24]1[C:29]([Cl:30])=[CH:28][CH:27]=[CH:26][C:25]=1[Cl:31])[CH3:18]>>[CH2:17]([O:19][C:20](=[O:41])[C@H:21]([CH2:33][C:34]1[CH:39]=[CH:38][C:37]([C:4]2[C:3]([O:2][CH3:1])=[CH:8][C:7]([CH2:9][CH2:10][OH:11])=[CH:6][C:5]=2[O:12][CH3:13])=[CH:36][CH:35]=1)[NH:22][C:23](=[O:32])[C:24]1[C:25]([Cl:31])=[CH:26][CH:27]=[CH:28][C:29]=1[Cl:30])[CH3:18]

Participants

3

Reactant 2

HCID 540252692,6-Dimethoxy-4-(2-hydroxyethyl)benzeneboronic acidHCID 54106344(S)-Ethyl 3-(4-bromophenyl)-2-(2,6-dichlorobenzamido)propanoate

Product 1

HCID 54075239N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-4-(2-hydroxyethyl)phenyl]-L-phenylalanine ethyl ester

Procedure

2,6-Dimethoxy-4-(2-hydroxyethyl)benzeneboronic acid was coupled with N-(2,6-dichlorobenzoyl)-4-bromo-L-phenylalanine ethyl ester according to the procedure described in Example 8-3) to yield 1.3 g of N-(2,6-dichlorobenzoyl)-4-[2,6-dimethoxy-4-(2-hydroxyethyl)phenyl]-L-phenylalanine ethyl ester. ESMS: m/z 546 (MH+).

Sources & evidence

ORD record
ord-8da01595314b4661810b4f23035bf727
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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