Methanol → HCID 15887091, compound

1.97 g L-DOPA (10 mmol) and 5 ml of dry methanol was added into an oven-dried 25 ml round-bottomed flask equipped with a Teflon stirring bar and rubber septum and purged with dry argon. Then, 1.3 ml of TMG (10 mmol) and 1.4 ml of methyl trifluoroacetate (12.5 mmol) was added. The mixture was stirred vigorously at room temperature until DOPA had completely dissolved (after about 24 hr). At this point, the flask was immersed in cold water (0° C.) and 5 ml of methanol and 4 g Dowex 50 resin (H+ form) were added. The mixture was filtered after stirring for 10 min. The filtrate was evaporated under reduced pressure. The crude product was re-crystallized from ethyl acetate and the yield of N-trifluoroacetyl-L-DOPA was 78%. See Curphey, T. J. Trifluoroacetylation of amino acids and peptides by ethyl trifluoroacetate. J. Org. Chem. 1979, 44, 2805-2807; Lapidot, Y.; Rappoport, S.; Wolman, Y. Use of ester of N-hydroxysuccinimide in the synthesis of N-acrylamino acids. J. Lipid Research 1967, 8, 142-145.

1. customequipped with a Teflon stirring bar
2. customrubber septum and purged with dry argon
3. dissolutionhad completely dissolved (after about 24 hr)
4. filtrationThe mixture was filtered
5. customThe filtrate was evaporated under reduced pressure
6. customThe crude product was re-crystallized from ethyl acetate
7. customUse of ester of N-hydroxysuccinimide in the synthesis of N-acrylamino acids

ORD record

ord-fe5eeb4ef7274174bc34df41eb878222

Source dataset

uspto-grants-2011_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08029774B2