Triphenylphosphine → 2-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(7-methoxy-2-phenyl-quinazolin-4-yloxy)-cyclopentanecarboxylic acid tert-butyl ester

Participants

Role	Name	HCID	Charge
Reactant	Triphenylphosphine	HCID 11776	—
Reactant	(1R,2R,4S)-2-((1R,2S)-1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl) 4-hydroxy-cyclopentanecarboxylic acid tert-butyl ester	HCID 59165438	—
Reactant	HCID 178487727	HCID 178487727	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	2-(1-Ethoxycarbonyl-2-vinyl-cyclopropylcarbamoyl)-4-(7-methoxy-2-phenyl-quinazolin-4-yloxy)-cyclopentanecarboxylic acid tert-butyl ester	HCID 68423072	68.1%

Reaction Conditions

Temperature	0 °C

Reaction Steps

Compound 35 (700 mg, 1.9 mmol), 7-methoxy-2-phenyl-quinazolin-4-ol (670 mg, 2.66 mmol) and triphenyl phosphine (1245 mg, 4.75 mmol) were dissolved in THF (50 ml) and cooled to 0° C. Diisopropyl azidocarboxylate (960 mg, 4.75 mmol) was added slowly and the slurry was allowed to reach room temperature. After 12 h, the solvent was removed under reduced pressure and the residue taken up in ether and filtrated. Purification by column chromatography (SiO2; 1% methanol in dichloromethane) gave the pure title compound (778 mg, 68%). MS (M+H+) 603.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07700552B2
Source dataset	uspto-grants-2010_04
ORD ID	ord-881ef959b0cc4a52a4513906db41bd54
Source note	uspto-grants-2010_04