2,6-Di(methoxymethoxy)benzeneboronic acid → N-(2,6-dichlorobenzoyl)-4-[2,6-di(methoxymethoxy)phenyl]-L-phenylalanine ethyl ester

HRID 24697Notes

Reaction equation

HRID 24697 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:12][O:13][CH3:14])[C:6]=1B(O)O.[CH2:18]([O:20][C:21](=[O:49])[C@H:22]([CH2:34][C:35]1[CH:40]=[CH:39][C:38](OS(C(F)(F)F)(=O)=O)=[CH:37][CH:36]=1)[NH:23][C:24](=[O:33])[C:25]1[C:30]([Cl:31])=[CH:29][CH:28]=[CH:27][C:26]=1[Cl:32])[CH3:19]>>[CH2:18]([O:20][C:21](=[O:49])[C@H:22]([CH2:34][C:35]1[CH:40]=[CH:39][C:38]([C:6]2[C:5]([O:4][CH2:3][O:2][CH3:1])=[CH:10][CH:9]=[CH:8][C:7]=2[O:11][CH2:12][O:13][CH3:14])=[CH:37][CH:36]=1)[NH:23][C:24](=[O:33])[C:25]1[C:26]([Cl:32])=[CH:27][CH:28]=[CH:29][C:30]=1[Cl:31])[CH3:19]

Participants

3

Reactant 2

HCID 225719952,6-Di(methoxymethoxy)benzeneboronic acidHCID 54080286HCID 54080286, compound

Product 1

HCID 54573164N-(2,6-dichlorobenzoyl)-4-[2,6-di(methoxymethoxy)phenyl]-L-phenylalanine ethyl ester

Procedure

2,6-Di(methoxymethoxy)benzeneboronic acid (0.25 g) was coupled with N-(2,6-dichlorobenzoyl)-O-(trifluoromethanesulfonyl)-L-tyrosine ethyl ester in a similar procedure as described in Example 5-3) to afford N-(2,6-dichlorobenzoyl)-4-[2,6-di(methoxymethoxy)phenyl]-L-phenylalanine ethyl ester. ESMS: m/z 562 (MH+).

Sources & evidence

ORD record
ord-399611d1bb7a456cbb4fdbdeec2e5319
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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