Triphenylphosphine → HCID 19909530, compound

Participants

Role	Name	HCID	Charge
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	Hydrazoic acid	HCID 24530	—
Reactant	11-Hydroxy-3-(1-hydroxy-3-methylbutyl)-4-methoxy-9-methyl-5H,7H-dibenzo[b,g][1,5]dioxocin-5-one	HCID 124213	—
Reactant	ethyl N-ethoxycarbonyliminocarbamate	HCID 220568	—
Solvent	Toluene	HCID 1140	—
Solvent	Dichloromethane	HCID 6344	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	HCID 19909530	HCID 19909530	—

Reaction Conditions

Temperature	25 °C

Reaction Steps

4.6 g (17.6 mmol) of triphenylphosphine and 29.3 ml of a freshly prepared 0.6 N solution of hydrazoic acid in toluene are added to 6 g (16.1 mmol) of penicillide (1b) in 100 ml of tetrahydrofuran. 2.7 ml (17.6 mmol) of diethyl azodicarboxylate are added dropwise to this mixture at 0° C. under argon. The mixture is then stirred at 25° C. for 12 h. After diluting with methylene chloride, the mixture is washed with aqueous bicarbonate, dried and evaporated. Chromatography on silica gel Si60 in diethyl ether/petroleum ether =2:1 yields 5.6 g (88% of theory) of colorless solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US05089487
Source dataset	uspto-grants-1992_02
ORD ID	ord-c234662dffc244a2b6992e641466fe03
Source note	uspto-grants-1992_02