Dimethyl Sulfoxide → HCID 57592135, compound

Temperature

0 °C

To a solution of oxalyl chloride (5.29 g, 41.4 mmol) in anhydrous dichloromethane (30 mL) at −78° C. was added anhydrous DMSO (6.2 mL, 87.4 mmol) dropwise with stirring in such a rate that the temperature was kept at −50 to −60° C. The solution was stirred for 15 min, then 2-fluoroethanol (1.62 mL, 27.6 mmol) was added dropwise and it was stirred for 15 min, diluted with dichloromethane (100 mL), followed by addition of dry Et3N (13.5 mL). The reaction mixture was stirred for 15 min, then allowed to warm to 0° C. and stirred at 0° C. for 2 h. To the reaction mixture was added a solution of 4-nitro-butyramide (3.04 g, 23 mmol) in CH2Cl2/THF (50 mL, 1:1). The reaction mixture was stirred at 0° C. for 3 h and then stirred at room temperature overnight. The mixture was concentrated to approximate 20 mL and poured into water (180 mL). It was extracted with ethyl acetate (12×40 mL), and the combined organic layers were dried and evaporated and the residue was purified by silica gel (CH2Cl2/EtOAc) to give 1.84 g (41%) of the titled product as a colorless viscous oil. 1H NMR (acetone-d6): 6.88 (bs, NH, 1H), 6.31 (bs, NH, 1H), 5.20-4.20 (m, 5H), 2.40-2.15 (m, 4H).

1. customwas kept at −50 to −60° C
2. stirringThe solution was stirred for 15 min
3. stirringit was stirred for 15 min
4. stirringThe reaction mixture was stirred for 15 min
5. stirringstirred at 0° C. for 2 h
6. stirringThe reaction mixture was stirred at 0° C. for 3 h
7. stirringstirred at room temperature overnight
8. concentrationThe mixture was concentrated to approximate 20 mL
9. additionpoured into water (180 mL)
10. extractionIt was extracted with ethyl acetate (12×40 mL)
11. customthe combined organic layers were dried
12. customevaporated
13. customthe residue was purified by silica gel (CH2Cl2/EtOAc)

ORD record

ord-d9eda4e4a48c457d943cfce1a204eb25

Source dataset

uspto-grants-2009_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07504382B2