(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

Participants

Role	Name	HCID	Charge
Reactant	(1-((2-(Trimethylsilyl)ethoxy)methyl)-1H-pyrazol-5-yl)boronic acid	HCID 21874652	—
Reactant	HCID 54123889	HCID 54123889	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	N-[4-[1-[[2-(trimethylsilyl)ethoxy]methyl]-5-pyrazolyl]-2,6-dichlorobenzoyl]-4-(2,6-dimethoxyphenyl)-L-phenylalanine methyl ester	HCID 54080883	95.6%

Reaction Steps

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)−.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US06855843B2
Source dataset	uspto-grants-2005_02
ORD ID	ord-38c196a2a6174a7eb0b9bb2dca61e137
Source note	uspto-grants-2005_02