Triethylamine → methyl N-tert-butoxycarbonylaminomethyl-salicylate

Methyl 4-aminomethylsalicylate hydrochloride (10.9 g, 50 mmoles) was suspended in anhydrous methanol (200 mL) and di-tert-butyldicarbonate (10.9 g, 50 mmoles) and triethylamine (7.0 mL, 50 mmoles) were added. The solid rapidly dissolved with the slow evolution of gas. The reaction mixture was stirred at room temperature for 18 hours under dry nitrogen, then evaporated to dryness to afford a white amorphous mass. This mass was partitioned between ethyl acetate (200 mL) and water (100 mL). The layers were separated, and the ethyl acetate solution was dried over anhydrous sodium sulfate. The solution was filtered and evaporated to a white solid. This solid was crystallized from ethyl acetate/hexanes, filtered, and dried in vacuo to afford 13.7 g (97% yield) of methyl N-tert-butoxycarbonylaminomethyl-salicylate (m.p. 95°-96° C., open capillary, uncorrected).

1. dissolutionThe solid rapidly dissolved with the slow evolution of gas
2. customevaporated to dryness
3. customto afford a white amorphous mass
4. customThis mass was partitioned between ethyl acetate (200 mL) and water (100 mL)
5. customThe layers were separated
6. dry with materialthe ethyl acetate solution was dried over anhydrous sodium sulfate
7. filtrationThe solution was filtered
8. customevaporated to a white solid
9. customThis solid was crystallized from ethyl acetate/hexanes
10. filtrationfiltered
11. customdried in vacuo

ORD record

ord-4b9ffb30ec5f481b98a1f008585a4b99

Source dataset

uspto-grants-1998_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05837878