(4-(1,3-Dioxolan-2-yl)-2,6-dimethoxyphenyl)boronic acid → N-(2,6-dichlorobenzoyl)-4-[4-(1,3-dioxolan-2-yl)-2,6-dimethoxyphenyl]-L-phenylalanine methyl ester

HRID 1060437Notes

Reaction equation

HRID 1060437 reaction equation
[O:1]1[CH2:5][CH2:4][O:3][CH:2]1[C:6]1[CH:11]=[C:10]([O:12][CH3:13])[C:9](B(O)O)=[C:8]([O:17][CH3:18])[CH:7]=1.[CH3:19][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][O:20][C:21](=[O:49])[C@H:22]([CH2:34][C:35]1[CH:36]=[CH:37][C:38]([C:9]2[C:10]([O:12][CH3:13])=[CH:11][C:6]([CH:2]3[O:3][CH2:4][CH2:5][O:1]3)=[CH:7][C:8]=2[O:17][CH3:18])=[CH:39][CH:40]=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]

Participants

3

Reactant 2

HCID 22571993(4-(1,3-Dioxolan-2-yl)-2,6-dimethoxyphenyl)boronic acidHCID 22970630HCID 22970630, compound

Product 1

HCID 54069836N-(2,6-dichlorobenzoyl)-4-[4-(1,3-dioxolan-2-yl)-2,6-dimethoxyphenyl]-L-phenylalanine methyl ester

Procedure

4-(1,3-Dioxolan-2-yl)-2,6-dimethoxybenzeneboronic acid was reacted with N-(2,6-dichlorobenzoyl)-O-(trifluoromethanesulfonyl)-L-tyrosine methyl ester in a similar manner as described in Example 7-2) to give N-(2,6-dichlorobenzoyl)-4-[4-(1,3-dioxolan-2-yl)-2,6-dimethoxyphenyl]-L-phenylalanine methyl ester.

Sources & evidence

ORD record
ord-ad33a321ebc344ebb418080f33c4eee1
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Reaction notes

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