Chloroacetyl chloride → HCID 90446601, compound

To a suspension of potassium carbonate (13.9 g, 100 mmol, 2.2 eq.) in water (33.5 mL) was added hydroxyazetidine hydrochloride (5 g, 45.6 mmol, 1 eq.). The reaction mixture was stirred at r.t. until complete dissolution, then diluted with 33.5 mL of DCM and cooled to 0° C. prior to the dropwise introduction of chloroacetyl chloride (4.4 mL, 54.8 mmol, 1.2 eq.) over 30 min After 2 h stirring at r.t., the reaction mixture was filtered, the organic layer was separated, and the aqueous phase was extracted with a mixture EtOAc/nBuOH 1:1 (6×16 mL). The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. The residue was suspended in acetone (48 mL) and stirred vigorously for 20 min, filtered and the filtrate was concentrated in vacuo to afford Intermediate Gen-13-a.

1. temperaturecooled to 0° C.
2. filtrationthe reaction mixture was filtered
3. customthe organic layer was separated
4. extractionthe aqueous phase was extracted with a mixture EtOAc/nBuOH 1:1 (6×16 mL)
5. dry with materialThe combined organic layers were dried over Na2SO4
6. filtrationfiltered
7. concentrationconcentrated in vacuo
8. stirringstirred vigorously for 20 min
9. filtrationfiltered
10. concentrationthe filtrate was concentrated in vacuo
11. customto afford Intermediate Gen-13-a

ORD record

ord-af6d8114cbc0451aa428869331784f15

Source dataset

uspto-grants-2016_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09249141B2