Phosphorus pentachloride → 1-Pentanesulfonyl chloride

To a solution of (4R)-4-[5-chloro-2-(acetoxymethyl)phenyl][4-chlorophenyl)sulfonyl]-amino]pentylsulfonic acid (560 mg, 1.07 mmol) in benzene (5 mL) was added phosphorus pentachloride (445 mg, 2.14 mmol) at 22° C. The mixture was heated to reflux for 2 hours. This mixture was concentrated under reduced pressure and rediluted with CH2Cl2 (100 mL). This solution was washed with water (100 mL), dried over Na2SO4 and filtered. The organic solution was concentrated to afford 442 mg of (4R)-4-[5-chloro-2-(acetoxymethyl)phenyl](4-chlorophenyl)sulfonyl]-amino]pentylsulfonyl chloride as a pale yellow oil in 76% yield.

1. temperatureThe mixture was heated
2. temperatureto reflux for 2 hours
3. concentrationThis mixture was concentrated under reduced pressure
4. additionrediluted with CH2Cl2 (100 mL)
5. washThis solution was washed with water (100 mL)
6. dry with materialdried over Na2SO4
7. filtrationfiltered
8. concentrationThe organic solution was concentrated

ORD record

ord-b087f401effe4cefac7bac300c01b5f2

Source dataset

uspto-grants-2005_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06967196B1