Sodium Hydroxide → HCID 93632892, compound

Temperature

75 °C

A 500-mL round bottomed flask equipped with a magnetic stir bar was charged with a solution of (S)-2-(5-bromo-3-nitropyridin-2-ylamino)propane-1-ol (6.8 g, 24.63 mmol) in ethanol (55 mL). Tin(II) chloride dihydrate (22.23 g, 99 mmol) was added, and the mixture was heated to 75° C. The dark orange color faded to a pale orange color over time. After 3 h, heating was discontinued. After the reaction mixture had cooled to ambient temperature, it was slowly diluted with 2 M sodium hydroxide solution (100 mL, 200 mmol). The thick slurry was further diluted with ethyl acetate. The biphasic mixture was rapidly stirred for 10-15 min, and then the organic layer was decanted into a separatory funnel. The small aqueous layer that carried with the ethyl acetate was drained, and the ethyl acetate extract was washed with 5% aqueous sodium chloride solution (2×100 mL). The original aqueous slurry was extracted with ethyl acetate, and the extract subsequently washed with the 5% aqueous sodium chloride solution. The combined ethyl acetate extracts were concentrated under reduced pressure. The biphasic residue was dissolved in acetonitrile (ca. 100 mL), which was then removed under reduced pressure. The process was repeated to yield crude (S)-2-(3-amino-5-bromopyridin-2-ylamino)propane-1-ol (5.95 g, 24.18 mmol, 98%) as a dark purple-green syrup, which eventually solidified upon standing. MS (ESI, pos. ion) m/z 246, 248 [M+1]+.

1. customA 500-mL round bottomed flask equipped with a magnetic stir bar
2. temperatureheating
3. temperatureAfter the reaction mixture had cooled to ambient temperature
4. customthe organic layer was decanted into a separatory funnel
5. extractionthe ethyl acetate extract
6. washwas washed with 5% aqueous sodium chloride solution (2×100 mL)
7. extractionThe original aqueous slurry was extracted with ethyl acetate
8. extractionthe extract subsequently
9. washwashed with the 5% aqueous sodium chloride solution
10. concentrationThe combined ethyl acetate extracts were concentrated under reduced pressure
11. dissolutionThe biphasic residue was dissolved in acetonitrile (ca. 100 mL)
12. customwhich was then removed under reduced pressure

ORD record

ord-99681416b423446983efac98d2f4274d

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09422281B2