Fmoc-4-nitro-L-phenylalanine
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Fmoc-4-nitro-L-phenylalanine
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CAS No:
95753-55-2
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Formula:
C24H20N2O6
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Chemical Name:
Fmoc-4-nitro-L-phenylalanine
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Synonyms:
FMOC-4-NITRO PHENYLALANINE;FMOC-4-NITRO-PHE-OH;9-FLUORENYLMETHOXYCARBONYL-P-NITRO-L-PHENYLALANINE;(S)-2-(FLUORENYLMETHOXYCARBONYLAMINO)-3-(4-NITROPHENYL)PROPANOIC ACID;RARECHEM BK PT 0075;N-ALPHA-FMOC-4-NITRO-L-PHENYLALANINE;N-[(9H-FLUOREN-9-YLMETHOXY)CARBONYL]-4-NITRO-L-PHENYLALANINE;N-ALPHA-(9-FLUORENYLMETHYLOXYCARBONYL)-L-4-NITROPHENYLALANINE
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CAS No:
Fmoc-4-nitro-L-phenylalanine Use and Manufacturing
A solution of 80 mL of acetonitrile was added to a suspension of 37.7 g (0.179 mol) of acid 2a and 2b in 200 mL of 2percent NaOH aqueous solution until complete dissolution. A solution of 61.8 g (0.183 mol) of suspension of Fmoc-OSu in 100 mL of acetonitrile was added to this solution. The reaction mixture was stirred for 3 hours at room temperature and acidified with 5percent HCl to pH 4-5. The precipitated white crystals were filtered off, washed with ethyl acetate, and dried. The reaction product was recrystallized from ethanol-dioxane mixture, 50 : 50. Yield 67percent (3a), 71percent (3b). mp 230°C (mp 233–234°C [10]). IR spectrum ν, cm–1: 3429, 3202, 1724, 1693, 1601, 1520, 1447, 1354, 1223, 1057, 856, 760, 741. 1 NMR spectrum (DMSO-d6), δ, ppm: 2.90–3.09 m (1H, CH2), 3.25 d.d (1H, CH2, 2J 13.7, 3J 4.3 Hz), 4.13–4.34 m (4H, 2CH2, 2CH), 7.23–7.45 m (4Harom), 7.54 d (2Harom, 3J 8.6 Hz), 7.60–7.64 m (2Harom), 7.79 d (1H, NH, 3J 8.6 Hz), 7.88 d (2Harom, 3J 7.5 Hz ), 8.14 d (2Harom, 3J 8.6 Hz ), 12.93 s (1H, COOH). 13 NMR spectrum (DMSO-d6), δ, ppm: 36.62 (CH2), 47.03 (CH), 55.25 (CH), 66.03 (CH2), 120.56, 123.69, 125.62, 127.45, 128.07, 130.94, 141.16, 144.20, 146.73 (arom), 156.39 (CONH), 173.27 (COOH). Mass spectrum (ESI), m/z: 455.1214 [M + Na]+. C24H20N2O6. Calculated M 432.1321.
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