Dimethyl Sulfoxide → HCID 118194672, compound

To a solution of (2R,3S)-2-benzyl-3((4-methoxybenzyl)oxy)butan-1-ol (5.38 g, 17.91 mmol) in CH2Cl2 (90 mL) in a nitrogen flushed 250 mL round bottomed flask was added DMSO (17.9 mL, 25.24 mmol) and TEA (12.5 mL, 90 mmol) via syringe followed by sulfur trioxode-pyridine complex (8.55 g, 53.7 mmol) in three equal portions at 0° C. under N2. The reaction was removed from the cold bath and allowed to warm to room temperature, and stirred for 2 h. The reaction was diluted with ice cold 0.5 N HCl (100 mL) and EtOAc (150 mL). The phases were separated and the organic phase was washed with sat. aq. NaHCO3 (50 mL) and brine (50 mL). The solution was dried over magnesium sulfate (MgSO4), filtered, and concentrated to afford the title compound (5.3 g, 96%) as a yellow oil: 1H NMR (400 MHz, CDCl3) δ 9.78 (d, J=2.8 Hz, 1H), 7.29-7.09 (m, 7H), 6.89 (d, J=8.7 Hz, 2H), 4.56 (d, J=11.3 Hz, 1H), 4.34 (d, J=11.3 Hz, 1H), 3.82 (s, 3H), 3.03 (dd, J=14.0, 8.2 Hz, 1H), 2.87 (dd, J=14.0, 6.4 Hz, 2H), 2.78-2.55 (m, 1H), 1.29 (d, J=6.4 Hz, 3H); ESIMS m/z 321.3 ([M+Na]+).

1. customfollowed by sulfur trioxode-pyridine complex (8.55 g, 53.7 mmol) in three equal portions at 0° C. under N2
2. customThe reaction was removed from the cold bath
3. additionThe reaction was diluted with ice cold 0.5 N HCl (100 mL) and EtOAc (150 mL)
4. customThe phases were separated
5. washthe organic phase was washed with sat. aq. NaHCO3 (50 mL) and brine (50 mL)
6. dry with materialThe solution was dried over magnesium sulfate (MgSO4)
7. filtrationfiltered
8. concentrationconcentrated

ORD record

ord-030e7eaad1894009b81aa9ed1953f247

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09247741B2