Diethyl Ether → HCID 68731586, compound

A mixture of 4-(tert-butoxycarbonylamino-methyl)-2-nitro-benzoic acid methyl ester (64.36 g, 207.4 mmol), lithium hydroxide (5.96 g, 248.9 mmol) in methanol (500 mL) and water (250 mL) was stirred with a mechanical stirrer at room temperature overnight. The methanol was evaporated, and to the aqueous solution, was added 1 N HCl (300 mL) to form the precipitate. Ether (350 mL) was added, and the mixture was stirred at 0° C. for 2 hours. No desired precipitation was formed. The mixture was evaporated. To the mixture, was added water (500 mL). The aqueous layer was extracted with ethyl acetate (5×120 mL). The combined organic layers were separated, dried over magnesium sulfate, and concentrated to give 4-(tert-butoxycarbonylamino-methyl)-2-nitro-benzoic acid as a brown oil (56.69 g, 92% yield). The product was used in the next step without further purification.

1. customThe methanol was evaporated
2. additionto the aqueous solution, was added 1 N HCl (300 mL)
3. customto form the precipitate
4. stirringthe mixture was stirred at 0° C. for 2 hours
5. customNo desired precipitation
6. customwas formed
7. customThe mixture was evaporated
8. additionTo the mixture, was added water (500 mL)
9. extractionThe aqueous layer was extracted with ethyl acetate (5×120 mL)
10. customThe combined organic layers were separated
11. dry with materialdried over magnesium sulfate
12. concentrationconcentrated

ORD record

ord-1d960fd8c6d1483c97dadd1398d77a50

Source dataset

uspto-grants-2015_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09096573B2