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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1669330Generated: October 31, 2026

Tributylphosphine → 3-{4-[1-(4-Bromo-3-methyl-phenyl)-5-methyl-hexyloxy]-benzoylamino}-propionic acid methyl ester

https://huagongshe.com/reaction/1669330

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTributylphosphineHCID 13831—
Reactant1,1'-(Azodicarbonyl)dipiperidineHCID 73042—
Reactant3-(4-Hydroxy-benzoylamino)-propionic acid methyl esterHCID 10632853—
Reactant1-(4-Bromo-3-methyl-phenyl)-5-methyl-hexan-1-olHCID 67345033—
SolventTolueneHCID 1140—
Product3-{4-[1-(4-Bromo-3-methyl-phenyl)-5-methyl-hexyloxy]-benzoylamino}-propionic acid methyl esterHCID 6734198263%

Reaction Steps

A solution of 3-(4-hydroxy-benzoylamino)-propionic acid methyl ester (805 mg, 3.61 mmol) and 1-(4-Bromo-3-methyl-phenyl)-5-methyl-hexan-1-ol (824 mg, 2.89 mmol) in toluene (15.0 mL) was degassed and filled with nitrogen for 3 times. Tributylphosphine (1.1 mL, 4.33 mmol) was added to the reaction mixture under nitrogen at 0° C., followed by addition of 1,1′-(azodicarbonyl)-dipiperidine (1.1 g, 4.33 mmol). The reaction mixture was allowed to warm to room temperature and stirred over night, the mixture was loaded on silica gel column. Chromatography gave the title compound (890 mg, 1.82 mmol).

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS07989457B2
Source datasetuspto-grants-2011_08
ORD IDord-66cc52cc37704c038a0a0c6c7c1ff829
Source noteuspto-grants-2011_08