BOC-L-4-Nitrophe synthesis
- Product Name:BOC-L-4-Nitrophe
- CAS Number:33305-77-0
- Molecular formula:C14H18N2O6
- Molecular Weight:310.3
24424-99-5
949-99-5
33305-77-0
To a stirred solution of 4.0 g of (S)-2-amino-3-(4-nitrophenyl)propanoic acid (0.019 mol) in 30 cm3 tert-butanol and 0.8 g of NaOH (0.0209 mol, dissolved in 5 cm3 of water) was added slowly and dropwise at 0 °C 5 cm3 of di-tert-butyl dicarbonate (0.0228 mol, dissolved in 5 cm3 of tert-butanol). The reaction mixture was stirred for 10 h at room temperature. After completion of the reaction (confirmed by thin layer chromatography), the solvent was removed by evaporation and the residue was poured into water and extracted with ethyl acetate (2 x 50 cm3). The organic phases were combined, washed sequentially with 50 cm3 10% citric acid solution and 50 cm3 saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give (S)-2-((tert-butoxycarbonyl)amino)-3-(4-nitrophenyl)propionic acid as a white solid. Yield: 5.0 g (86% yield); Melting point: 105-106°C (literature value 105-107°C).
24424-99-5
867 suppliers
$13.50/25G
949-99-5
370 suppliers
$11.00/1g
33305-77-0
269 suppliers
$6.00/5g
Yield:33305-77-0 88%
Reaction Conditions:
in tetrahydrofuran;sodium hydroxide
Steps:
48.A (S)-N-boc-4-nitrophenylalanine
Example 48A (S)-N-boc-4-nitrophenylalanine To a solution of (S)-4-nitrophenylalanine (2.00 g, 9.51 mmol) in aqueous 2M NaOH (10 mL) and THF (5 mL), was added di-tertbutyldicarbonate (2.00 g, 9.17 mmol) in THF (5 mL). The reaction was stirred at ambient temperature for 1 hour, diluted with H2O (25 mL) and 1M HCl (25 mL), extracted with ether (3*25 mL). The combined ether layers were extracted with brine (1*25 mL), dried (MgSO4), filtered, and concentrated under reduced pressure to provide the titled compound (2.51 g, 88%).
References:
Liu, Gang;Szczepankiewicz, Bruce G.;Pei, Zhonghua;Xin, Zhili;Oost, Thorsten K.;Janowick, David A. US2002/35137, 2002, A1
65615-89-6
53 suppliers
$120.00/250mg
33305-77-0
269 suppliers
$6.00/5g
74-96-4
458 suppliers
$9.00/5g
24424-99-5
867 suppliers
$13.50/25G
949-99-5
370 suppliers
$11.00/1g
33305-77-0
269 suppliers
$6.00/5g
