Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester → Methyl (2E)-((1R,4R,5S,8S,12R)-7-(4-cyano-3-(trifluoromethyl)phenyl)-4-methyl-6-oxo-9,13-dioxa-7-azatetracyclo[6.3.1.11,4.05,12]tridec-2-ylidene)acetate

Participants

Role	Name	HCID	Charge
Reactant	Acetic acid, 2-(triphenylphosphoranylidene)-, methyl ester	HCID 17453	—
Reactant	Benzonitrile, 4-((3aR,4S,6R,6aS,8aS,8bR)-octahydro-4-hydroxy-6-methyl-7-oxo-3a,6-epoxy-3ah-pyrano(2,3,4-cd)isoindol-8(4H)-yl)-2-(trifluoromethyl)-	HCID 59635881	—
Solvent	Tetrahydrofuran	HCID 8028	—
Product	Methyl (2E)-((1R,4R,5S,8S,12R)-7-(4-cyano-3-(trifluoromethyl)phenyl)-4-methyl-6-oxo-9,13-dioxa-7-azatetracyclo[6.3.1.11,4.05,12]tridec-2-ylidene)acetate	HCID 86649395	71%

Reaction Steps

To a solution of Example 3 (50 mg, 0.128 mmol) in THF (2 mL) was added methyl(triphenylphosphoranylidene)acetate (51 mg, 0.153 mmol). The reaction mixture was stirred for 3 days and then concentrated in vacuo. The resulting residue was purified by ISCO column (4.0 g column, EtOAc/hexane=0-80%, 10 mL/min) to give Example 103 (40.5 mg, 71%) as a yellow solid.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US08067582B2
Source dataset	uspto-grants-2011_11
ORD ID	ord-df01495722c646e3b6e55dacaddd1cdc
Source note	uspto-grants-2011_11