Nitrogen → (2S,3R)-Methyl 2-(4-((4-formylphenyl)ethynyl)benzamido)-3-hydroxybutanoate

Participants

Role	Name	HCID	Charge
Reactant	Nitrogen	HCID 947	—
Reactant	Tetrahydrofuran	HCID 8028	—
Reactant	Triethylamine	HCID 8471	—
Reactant	2-[(tert-butoxy)carbonylamino]-N-(4-iodophenyl)acetamide	HCID 47451239	—
Reactant	methyl(2S,3R)-3-hydroxy-2-{[4-(phenylcarbonyl)phenyl]carbonylamino}butanoate	HCID 59697585	—
Catalyst	Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)	HCID 24350	—
Catalyst	HCID 178418476	HCID 178418476	—
Product	(2S,3R)-Methyl 2-(4-((4-formylphenyl)ethynyl)benzamido)-3-hydroxybutanoate	HCID 59697530	80%

Reaction Steps

A solution of alkyne 1 (745 mg, 2.85 mmol), 4-iodobenzaldehyde 2 (902 mg, 3.89 mmol), and Et3N (900 μL, 6.5 mmol) in THF (50 mL) was purged with a stream of N2 for two minutes and then treated with PdCl2(PPh3)2 (70 mg, 0.10 mmol) and CuI (34 mg, 0.18 mmol). The reaction mixture was stirred 40 h, concentrated by rotary evaporation and purified by silica gel chromatography (40:1 DCM/MeOH) to give 0.833 g (80% yield) of (2S,3R)-2-[4-(4-formyl-phenylethynyl)-benzoylamino]-3-hydroxy-butyric acid methyl ester 3 as a pale yellow powder, mp=143-144° C. Rf=0.3 (25:1 DCM/MeOH); LRMS (ES+) m/z 366.1 (C21H19NO5+H requires 366.13); HPLC (300 nm, 47 min) 15.3 min.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08153843B2
Source dataset	uspto-grants-2012_04
ORD ID	ord-fcbae179af35405ea597f969f4158c40
Source note	uspto-grants-2012_04