Sodium Hydroxide → HCID 178465665, compound

Temperature

0 °C

Sodium hydroxide (16.0 g, 400 mmol) was dissolved in absolute ethanol (1000 mL) at 60° C. The solution was cooled to 0° C., and treated portion-wise with ethyl ethanimidoate hydrochloride (50 g, 400 mmol); after 10 minutes, tert-butyl hydrazinecarboxylate (52.9 g, 400 mmol) was added in a single portion. The reaction was warmed to 70° C. and was stirred at 70° C. for 2.5 hours. The mixture was then cooled to 20° C. and filtered. The filtrate was concentrated in vacuo and treated with tert-butyl methyl ether (500 mL) and ethanol (20 mL). After seeding, the mixture was allowed to stir for 18 hours, after which time the precipitated solid was collected via filtration and washed with ice-cold tert-butyl methyl ether (500 mL). The solid was dissolved in 2-methyltetrahydrofuran:methanol (9:1 mixture, 300 mL), and the solution was concentrated to dryness. The residue was washed with diethyl ether (3×200 mL) and dried, affording the product as a very pale yellow solid. Yield; 50.2 g, 290 mmol, 72%. LCMS m/z 174.3 (M+1). 1H NMR (500 MHz, CD3OD) δ 1.47 (s, 9H), 1.88 (s, 3H).

1. temperatureThe reaction was warmed to 70° C.
2. temperatureThe mixture was then cooled to 20° C.
3. filtrationfiltered
4. concentrationThe filtrate was concentrated in vacuo
5. additiontreated with tert-butyl methyl ether (500 mL) and ethanol (20 mL)
6. stirringto stir for 18 hours
7. filtrationafter which time the precipitated solid was collected via filtration
8. washwashed with ice-cold tert-butyl methyl ether (500 mL)
9. dissolutionThe solid was dissolved in 2-methyltetrahydrofuran:methanol (9:1 mixture, 300 mL)
10. concentrationthe solution was concentrated to dryness
11. washThe residue was washed with diethyl ether (3×200 mL)
12. customdried
13. customaffording the product as a very pale yellow solid

ORD record

ord-c7d6ff4123ab4dd8ba56b2bcb76b2e03

Source dataset

uspto-grants-2013_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08598155B2