Water → HCID 67233299, compound

Temperature

-78 °C

Under a nitrogen atmosphere, lithium hexamethyldisilazide (2.4 mL, 2.4 mmol) was mixed with THF (5 mL). The reaction was cooled to −78° C. 1,4-cyclohexane-dione monoethylene acetal (374 mg, 2.4 mmol), dissolved in THF (2 mL) was slowly added via dropping funnel. The reaction was stirred for 20 min at −78° C. It was then cannulated to a flask, cooled at −78° C., containing benzothiazole-6-carbonyl chloride (498 mg, 2.52 mmol) dissolved in THF (5 mL). After the addition, the reaction was stirred at −78° C. for 1 hr, and then allowed to warm to room temperature. After 12 h, water (30 mL) was added and extracted with ethyl acetate (3×20 mL). The combined organic layers were washed with 10% citric acid (20 mL), water (20 mL), bicarb (20 mL), and brine (20 mL). It was then dried over Na2SO4, filtered and concentrated in vacuo. The crude material was purified by silica gel column (1:1 EtOAc/Hexanes) to yield 7-(Benzothiazole-6-carbonyl)-1,4-dioxa-spiro[4.5]decan-8-one (271 mg, 35%, light yellow solid).

1. additionwas slowly added
2. customIt was then cannulated to a flask
3. temperaturecooled at −78° C.
4. additionAfter the addition
5. stirringthe reaction was stirred at −78° C. for 1 hr
6. temperatureto warm to room temperature
7. waitAfter 12 h
8. extractionextracted with ethyl acetate (3×20 mL)
9. washThe combined organic layers were washed with 10% citric acid (20 mL), water (20 mL), bicarb (20 mL), and brine (20 mL)
10. dry with materialIt was then dried over Na2SO4
11. filtrationfiltered
12. concentrationconcentrated in vacuo
13. customThe crude material was purified by silica gel column (1:1 EtOAc/Hexanes)

ORD record

ord-ea99e469a9a14b0cbd0cf880a9ef7341

Source dataset

uspto-grants-2015_02

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08957105B2