ChemicalBook CAS DataBase List 4-(Aminocarbonyl)-N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-L-phenylalanine

4-(Aminocarbonyl)-N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-L-phenylalanine synthesis

7synthesis methods

Product Name:4-(Aminocarbonyl)-N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-L-phenylalanine
CAS Number:623950-02-7
Molecular formula:C17H24N2O5
Molecular Weight:336.38

623950-05-0 Synthesis

4'-carbamoyl N-Boc-2',6'-dimethyl-L-phenylalanine methyl ester

623950-05-0
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4-(Aminocarbonyl)-N-[(1,1-dimethylethoxy)carbonyl]-2,6-dimethyl-L-phenylalanine

623950-02-7
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$16.00/250mg

Yield:623950-02-7 94%

Reaction Conditions:

with lithium hydroxide;water in tetrahydrofuran;

Steps:

15.G (S)-2-tert-Butoxycarbonylamino-3-(4-carbamoyl-2,6-dimethyl-phenyl)-propionic acid

G. (S)-2-tert-Butoxycarbonylamino-3-(4-carbamoyl-2,6-dimethyl-phenyl)propionic acid. Into an ice-cooled solution of Compound 8c (0.22 g, 0.63 mmol) in THF (3.5 mL) was added an aqueous LiOH solution (1 N, 3.5 mL) and stirred at 0° C. Upon completion of the reaction, the reaction was concentrated and the aqueous phase was neutralized with cooled aqueous 1 N HCl at 0° C., and extracted with EtOAc. The combined extracts were dried over Na₂SO₄ overnight. Filtration and evaporation of the filtrate to dryness led to Compound 8d (0.20 g, 94%) as a white solid. ¹H NMR (300 MHz, DMSO-d₆): δ 1.30 (9H, s), 2.32 (6H, s), 2.95(1H, dd, J=8.8, 13.9 Hz), 3.10 (1H, dd, J=6.2, 14.0 Hz), 4.02-4.12 (1H, m), 7.18-7.23 (2H, m), 7.48 (2H, s), 7.80 (1H, s); MS(ES⁺) (relative intensity): 236.9 (6) (M-Boc)⁺.

References:

US2005/203143,2005,A1 Location in patent:Page/Page column 46

1227311-10-5 Synthesis