(Diethylamino)sulfur trifluoride → HCID 23594044, compound

Temperature

-78 °C

To a solution of diethylaminosulfur trifluoride (0.073 mL, 0.45 mmol) in CH2Cl2 (2 mL) cooled at −78° C. in a flame-dried flask under argon was added dropwise a solution of 6C (92 mg, 0.3 mmol) in CH2Cl2 (12 mL). After addition, the reaction mixture was stirred at −78° C. for 30 min, then at 0° C. overnight. The reaction mixture was partitioned between CH2Cl2 and saturated aqueous NaHCO3. The separated aqueous layer was extracted with CH2Cl2 (2×). The combined CH2Cl2 layers were washed with brine, dried over Na2SO4 and filtered. The filtrate was concentrated under reduced pressure to give a crude product, which was chromatographed (silica gel) eluting with EtOAc/hexane (1:2) to give 52 mg of the title compound (racemate) as a white solid. m.p. 228-230° C.; HPLC: 99% at 5.0 min (retention time) (Conditions: Zorbax SB C18 (4.6×75 mm); Eluted with 0% to 100% B, 8 min gradient. (A=90% H2O−10% MeOH−0.1% H3PO4 and B=10% H2O−90% MeOH−0.1% H3PO4); Flow rate at 2.5 mL/min. UV detection at 220 nm). MS (ES): m/z 641 [2M+Na]+.

1. additionAfter addition
2. customat 0° C.
3. customovernight
4. customThe reaction mixture was partitioned between CH2Cl2 and saturated aqueous NaHCO3
5. extractionThe separated aqueous layer was extracted with CH2Cl2 (2×)
6. washThe combined CH2Cl2 layers were washed with brine
7. dry with materialdried over Na2SO4
8. filtrationfiltered
9. concentrationThe filtrate was concentrated under reduced pressure
10. customto give a crude product, which
11. customwas chromatographed (silica gel)
12. washeluting with EtOAc/hexane (1:2)

ORD record

ord-9dc39e13c0144cd5994cb2ea6b2e02b9

Source dataset

uspto-grants-2003_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06670386B2