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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1914309Generated: November 2, 2026

Triethylamine → 3-{4-[1-(4-Bromo-phenoxy)-heptyl]-benzoylamino}-propionic acid methyl ester

https://huagongshe.com/reaction/1914309

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
ReactantMethyl beta-alanateHCID 192794—
Reactant4-[1-(4-Bromo-phenoxyl)-heptyl]-benzoic acidHCID 67153429—
Catalyst4-(Dimethylamino)pyridineHCID 14284—
SolventDichloromethaneHCID 6344—
Product3-{4-[1-(4-Bromo-phenoxy)-heptyl]-benzoylamino}-propionic acid methyl esterHCID 6715338780.1%

Reaction Steps

To a mixture of 4-[1-(4-bromo-phenoxyl)-heptyl]-benzoic acid (1700 mg, 4.35 mmol) in methylene chloride (43 mL) are added triethyl amine (1.82 mL, 13.4 mmol), DMAP (5.0 mg), 3-amino-propionic acid methyl ester (910 mg, 6.52 mmol) and EDCI (2507 mg, 13.04 mmol) at room temperature. The reaction mixture is stirred at room temperature overnight, loaded on silica gel, eluted with eluted with hexanes with a gradient from 0% of ethyl acetate to 100% of ethyl acetate giving racemic 3-{4-[1-(4-bromo-phenoxyl)-heptyl]-benzoylamino}-propionic acid methyl ester (1660 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08609892B2
Source datasetuspto-grants-2013_12
ORD IDord-d1234ec8e02c459f9566f94e20091c8b
Source noteuspto-grants-2013_12