Triphenylphosphine → HCID 86687286, compound

Participants

Role	Name	HCID	Charge
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	2-(Oxan-2-yloxy)ethan-1-ol	HCID 4166833	—
Reactant	Diisopropyl azodicarboxylate	HCID 5363146	—
Reactant	3-{5-Amino-3-[2-(tert-butyl-diphenyl-silanyloxy)-1,1-dimethyl-ethyl]-pyrazol-1-yl}-phenol	HCID 86687285	—
Solvent	Water	HCID 962	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	HCID 86687286	HCID 86687286	61.3%

Reaction Conditions

Temperature	0 °C

Reaction Steps

A mixture of Intermediate 153d (0.53 g, 1.09 mmol) in dry THF (8 mL) was treated with triphenylphosphine (0.57 g, 2.18 mmol) and 2-(tetrahydro-2H-pyran-2-yloxy)ethanol (0.22 mL, 1.64 mmol). The mixture was cooled to 0° C. then diisopropylazodicarboxylate (0.43 mL, 2.18 mmol) was added dropwise. After stirring at ambient temperature for 20 h the mixture was treated with water (0.1 mL) and concentrated in vacuo to a yellow oil. The oil was purified by FCC, using 0-30% EtOAc in cyclohexane, to give the title compound as an orange oil (0.41 g, 61%). LCMS (Method 3): Rt 5.25 min, m/z 614.6 [MH+].

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08907094B2
Source dataset	uspto-grants-2014_12
ORD ID	ord-867bc755914d451bbd9ca9702db02b88
Source note	uspto-grants-2014_12