Dimethyl Sulfoxide → HCID 18404487, compound

Temperature

0 °C

A solution of 0.2 mL (2.2 mmol) of oxalyl chloride in 4 mL of CH2Cl2 at −78° C. was treated with 0.32 mL (4.5 mmol) of DMSO in 0.5 mL of CH2Cl2 maintaining the temperature at less than 60° C. The resulting mixture was stirred cold for 5 min. A solution of 211 mg (0.94 mmol) of 2,2-dimethyl-3-hydroxypropionic acid, para-methoxybenzyl ester (from Step A) in 1 mL of CH2Cl2 was added maintaining the temperature at less than −60° C. The resulting mixture was stirred cold for 15 min. The mixture was treated with 1.6 mL (9.1 mmol) of DIEA maintaining the temperature at less than −60° C. The reaction was warmed to 0° C., stirred for 30 min and quenched with H2O. The mixture was partitioned between 50 mL of CH2Cl2 and 50 mL of H2O and the layers were separated. The aqueous layer was extracted with 50 mL of CH1Cl2. The combined organic phases were washed with 100 mL of brine, dried over Na2SO4 and concentrated to afford the title compound which was used without further purification: RF: 0.43 (4:1 v/v hexanes/EtOAc); 1H-NMR (500 MHz) δ 1.35 (s, 6H), 3.81 (s, 3H), 5.12 (s, 2H), 6.89 (d, J=8.7, 2H), 7.27 (d, J=8.7, 2H), 9.66 (s, 1H).

1. temperaturemaintaining the temperature at less than −60° C
2. stirringThe resulting mixture was stirred cold for 15 min
3. stirringstirred for 30 min
4. customquenched with H2O
5. customThe mixture was partitioned between 50 mL of CH2Cl2 and 50 mL of H2O
6. customthe layers were separated
7. extractionThe aqueous layer was extracted with 50 mL of CH1Cl2
8. washThe combined organic phases were washed with 100 mL of brine
9. dry with materialdried over Na2SO4
10. concentrationconcentrated

ORD record

ord-e134ba7bbf87422eb8fbf3010177c1fd

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07125887B2