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HuagongsheHuagongshe Chemistry Print Report · For research reference only
HRID 1691537Generated: November 2, 2026

Tributylphosphine → Methyl 2-[4-({4-[((3-methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]benzyl}oxy)phenyl]cyclopropanecarboxylate

https://huagongshe.com/reaction/1691537

Reaction equation

Participants

RoleNameHCIDCharge
ReactantTributylphosphineHCID 13831—
Reactant1,1'-(Azodicarbonyl)dipiperidineHCID 73042—
Reactant{4-[((3-Methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]phenyl}methanolHCID 23157500—
ReactantMethyl 2-(4-hydroxyphenyl)cyclopropane-1-carboxylateHCID 59364069—
SolventTolueneHCID 1140—
SolventHexaneHCID 8058—
ProductMethyl 2-[4-({4-[((3-methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}amino)methyl]benzyl}oxy)phenyl]cyclopropanecarboxylateHCID 5936406746.2%

Reaction Steps

A solution of methyl 2-(4-hydroxyphenyl)cyclopropanecarboxylate (0.152 g, 0.790 mmol), {4-[((3-methylbutyl){4-[4-(trifluoromethyl)phenyl]-1,3- thiazol-2-yl}amino)methyl]phenyl}methanol (0.312 g, 0.718 mmol) and tributylphosphine (0.291 g, 1.44 mmol) in toluene (15 mL) was stirred, 1,1′-(azodicarbonyl)dipiperidine (0.363 g, 1.44 mmol) was added, and the mixture was stirred at room temperature for 60 hr. Hexane (15 mL) was added to the reaction mixture, and the precipitated insoluble material was filtrated. The filtrate was concentrated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate:hexane=0:100-30:70) to give the title compound (0.202 g, yield 42%) as a colorless oil.

Provenance & Evidence

DOI10.6084/m9.figshare.5104873.v1
Patent numberUS08153694B2
Source datasetuspto-grants-2012_04
ORD IDord-d231ac9ac7164a6595a53f67d540ef30
Source noteuspto-grants-2012_04