Triethylamine → 4-Hydroxy-3-(5-hydroxymethyl-2-isopropyl-thiophen-3-ylsulfanyl)-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-one

The title compound was prepared according to General Method 16b using 4-hydroxy-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-one (Example E-20; 0.200 g, 0.75 mmol), toluene-4-thiosulfonic acid S-[5-(tert-butyl-dimethyl-silanyloxymethyl)-2-isopropyl-thiophen-3-yl]ester (Example BB-9; 0.377 g, 0.83 mmol), NEt3 (0.209 mL, 1.50 mmol), and acetonitrile (1.5 mL). As part of the purification, the silylether was cleaved by dissolving the crude coupled product in THF (50 mL) and then treated with a 1.0 M THF solution of tetrabutylammoniumflouride (1.5 mL, 1.5 mmol). After 30 minutes, the mixture was diluted with H2O and extracted with EtOAc. The organic layers were then combined, dried (MgSO4), and concentrated. The resulting residue was then submitted to column chromatography (eluting with 3% MeOH in CH2Cl2) to provide the title compound, mp 52-54° C.

1. customThe title compound was prepared
2. customAs part of the purification
3. dissolutionby dissolving the crude
4. extractionextracted with EtOAc
5. dry with materialdried (MgSO4)
6. concentrationconcentrated
7. washThe resulting residue was then submitted to column chromatography (eluting with 3% MeOH in CH2Cl2)

ORD record

ord-5ce9fcff9ef043ae914e9fd2b86977c5

Source dataset

uspto-grants-2005_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06852711B2