6-Methoxy-2-methoxymethoxybenzeneboronic acid → N-(2,6-dichlorobenzoyl)-4-(6-methoxy-2-methoxymethoxyphenyl)-L-phenylalanine ethyl ester

HRID 24674Notes

Reaction equation

HRID 24674 reaction equation
[CH3:1][O:2][C:3]1[C:8](B(O)O)=[C:7]([O:12][CH2:13][O:14][CH3:15])[CH:6]=[CH:5][CH:4]=1.[CH2:16]([O:18][C:19](=[O:47])[C@H:20]([CH2:32][C:33]1[CH:38]=[CH:37][C:36](OS(C(F)(F)F)(=O)=O)=[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:47])[C@H:20]([CH2:32][C:33]1[CH:38]=[CH:37][C:36]([C:8]2[C:3]([O:2][CH3:1])=[CH:4][CH:5]=[CH:6][C:7]=2[O:12][CH2:13][O:14][CH3:15])=[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 225716526-Methoxy-2-methoxymethoxybenzeneboronic acidHCID 54080286HCID 54080286, compound

Product 1

HCID 54508489N-(2,6-dichlorobenzoyl)-4-(6-methoxy-2-methoxymethoxyphenyl)-L-phenylalanine ethyl ester

Procedure

6-Methoxy-2-methoxymethoxybenzeneboronic acid (1.92 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-(6-methoxy-2-methoxymethoxyphenyl)-L-phenylalanine ethyl ester (0.942 mg). ESMS m/Z 532 (MH+), 530 (M−H)−.

Sources & evidence

ORD record
ord-393f370bd5f5429bbdc16c0f09d079e2
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Reaction notes

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