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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1436205Generated: October 26, 2026

Ethyl bromoacetate → (S)-3-chloro-N-(4-hydroxy-1-(4-(1-methyl-2-(2-methyl-1,3-dioxolan-2-yl)-1H-imidazol-4-yl)phenyl)butan-2-yl)-4-isopropoxybenzamide

https://huagongshe.com/reaction/1436205

Reaction equation

Participants

RoleNameHCIDCharge
ReactantEthyl bromoacetateHCID 7748—
ReactantPotassium CarbonateHCID 11430—
Reactant(S)-3-chloro-N-(4-hydroxy-1-(4-(2-(1-(hydroxyimino)ethyl)-1-methyl-1H-imidazol-4-yl)phenyl)butan-2-yl)-4-isopropoxybenzamideHCID 136388607—
SolventWaterHCID 962—
SolventDimethylformamideHCID 6228—
Product(S)-3-chloro-N-(4-hydroxy-1-(4-(1-methyl-2-(2-methyl-1,3-dioxolan-2-yl)-1H-imidazol-4-yl)phenyl)butan-2-yl)-4-isopropoxybenzamideHCID 5759471391%

Reaction Conditions

Temperature60 °C

Reaction Steps

To a solution of compound 3 (2.66 g, 7.27 mmol) in DMF (15 mL) was added K2CO3 (2.00 g, 15 mmol) and ethyl bromoacetate (1.61 mL, 14.5 mmol). The resulting mixture was stirred at 60° C. for three hours. The mixture was diluted with water and extracted with EtOAc (3×50 mL). The organic layers were combined, dried over Na2SO4, and concentrated. Purification with column chromatography (Hexanes/EtOAc 50:50) gave the product 4 (3.02 g, 91%).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07618981B2
Source datasetuspto-grants-2009_11
ORD IDord-e563ddcf23c24d3ca4199467586442fb
Source noteuspto-grants-2009_11