(1-((2-(Trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)boronic acid → N-[4-[1-[[2-(trimethylsilyl)ethoxy]methyl]-5-pyrazolyl]-2,6-dichlorobenzoyl]-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl ester

HRID 1060460Notes

Reaction equation

HRID 1060460 reaction equation
[CH3:1][O:2][C:3](=[O:34])[C@H:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:29]([O:30][CH3:31])=[CH:28][CH:27]=[CH:26][C:25]=2[O:32][CH3:33])=[CH:20][CH:19]=1)[NH:5][C:6](=[O:16])[C:7]1[C:12]([Cl:13])=[CH:11][C:10](Br)=[CH:9][C:8]=1[Cl:15].[CH3:35][Si:36]([CH3:50])([CH3:49])[CH2:37][CH2:38][O:39][CH2:40][N:41]1[C:45](B(O)O)=[CH:44][CH:43]=[N:42]1>C1COCC1>[CH3:1][O:2][C:3](=[O:34])[C@H:4]([CH2:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[C:29]([O:30][CH3:31])=[CH:28][CH:27]=[CH:26][C:25]=2[O:32][CH3:33])=[CH:20][CH:19]=1)[NH:5][C:6](=[O:16])[C:7]1[C:12]([Cl:13])=[CH:11][C:10]([C:45]2[N:41]([CH2:40][O:39][CH2:38][CH2:37][Si:36]([CH3:50])([CH3:49])[CH3:35])[N:42]=[CH:43][CH:44]=2)=[CH:9][C:8]=1[Cl:15]

Participants

4

Reactant 2

HCID 21874652(1-((2-(Trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)boronic acidHCID 54123889HCID 54123889, compound

Product 1

HCID 54080883N-[4-[1-[[2-(trimethylsilyl)ethoxy]methyl]-5-pyrazolyl]-2,6-dichlorobenzoyl]-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl esterYield 95.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-Bromo-2,6-dichlorobenzoyl)-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl ester (0.240 g) was coupled with 1-[[2-(trimethylsilyl)ethoxy]methyl]-5-pyrazoleboronic acid (0.343 g) in THF (10 mL) as described in Example 7-2) to give N-[4-[1-[[2-(trimethylsilyl)ethoxy]methyl ]-5-pyrazolyl]-2,6-dichlorobenzoyl]-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl ester (0.277 g). ESMS: m/z 684 (MH+) and 682 (M−H)−.

Sources & evidence

ORD record
ord-8d4db926b1bb4ced97095b373c8893ef
Source dataset
uspto-grants-2003_02
Patent number
US06521666B1

Reaction notes

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