Water → HCID 86704408, compound

A cold (−78° C.) solution of oxalyl chloride (0.58 mL, 6.7 mmol) in dichloromethane (13 mL) was treated with the dropwise addition of DMSO (0.74 mL) in dichloromethane (4 mL). After 2 minutes, I-13C (684 mg, 6.10 mmol) in dichloromethane (8 mL) was introduced. After 15 minutes, triethylamine (4.25 mL) was introduced dropwise. The reaction was then warmed to room temperature and diluted with dichloromethane and water. The organic phase was collected and washed with 1N HCl (aq.), water, saturated Na2CO3 (aq.), water, and brine. The organic phase was dried (MgSO4), filtered, and concentrated. The crude material was taken upon in ethanol (10 mL) and treated with 50% hydroxylamine (0.56 mL). After overnight stirring, the reaction was concentrated in vacuo. This residue was diluted with DMF (3.5 mL) and cooled to 0° C. NCS (0.91 g, 6.8 mmol) was introduced and the reaction slowly warmed to room temperature and stirred for 2 hours. The reaction was treated with saturated NaCl (aq.) and extracted with Et2O. Organics were washed with brine and then dried (MgSO4), filtered, and concentrated. MS m/z 160.1 (M+1).

1. waitAfter 15 minutes
2. customThe organic phase was collected
3. washwashed with 1N HCl (aq.), water, saturated Na2CO3 (aq.), water, and brine
4. dry with materialThe organic phase was dried (MgSO4)
5. filtrationfiltered
6. concentrationconcentrated
7. additiontreated with 50% hydroxylamine (0.56 mL)
8. concentrationthe reaction was concentrated in vacuo
9. additionThis residue was diluted with DMF (3.5 mL)
10. temperaturecooled to 0° C
11. customthe reaction
12. temperatureslowly warmed to room temperature
13. stirringstirred for 2 hours
14. extractionextracted with Et2O
15. washOrganics were washed with brine
16. dry with materialdried (MgSO4)
17. filtrationfiltered
18. concentrationconcentrated

ORD record

ord-ab37c3da6a624ad2b0a2f1e7fdcbc9f7

Source dataset

uspto-grants-2015_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09150568B2