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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1160903Generated: November 1, 2026

Triethylamine → 3-{4-[1-(4'-tert-butyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-2(R)-hydroxy-propionic acid methyl ester

https://huagongshe.com/reaction/1160903

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTriethylamineHCID 8471—
Reactant1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 15908—
Reactantmethyl (2R)-3-amino-2-hydroxypropanoateHCID 11665404—
Reactant4-[1-(4'-Tertbutyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoic acidHCID 67153528—
Catalyst4-(Dimethylamino)pyridineHCID 14284—
SolventDichloromethaneHCID 6344—
Product3-{4-[1-(4'-tert-butyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-2(R)-hydroxy-propionic acid methyl esterHCID 6715354140.2%

Reaction Steps

To a mixture of 4-[1-(4′-tertbutyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoic acid (120 mg) in methylene chloride (3 mL) are added triethyl amine (0.12 mL, 0.87 mmol), DMAP (5 mg), 3-Amino-2(R)-hydroxy-propionic acid methyl ester (67.3 mg, 0.43 mmol) and EDCI (166 mg, 0.87 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 3-{4-[1-(4′-tert-butyl-biphenyl-4-yloxy)-3-methyl-butyl]-benzoylamino}-2(R)-hydroxy-propionic acid methyl ester (60 mg).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07816557B2
Source datasetuspto-grants-2010_10
ORD IDord-f7fb059fe4f648c581fe4c7dd5a43f0f
Source noteuspto-grants-2010_10