3-AMINO-3-(THIOPHEN-3-YL)PROPANOIC ACID synthesis
- Product Name:3-AMINO-3-(THIOPHEN-3-YL)PROPANOIC ACID
- CAS Number:94333-62-7
- Molecular formula:C7H9NO2S
- Molecular Weight:171.21
498-62-4
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Yield:94333-62-7 72%
Reaction Conditions:
with ammonium acetate in ethanol; for 7 h;Reflux;
Steps:
Compound 2. (+/-)-3-Amino-3-(thiophen-3-yl)propanoic acid.
A solution of thiophen-3-carbaldehyde (2.00 g, 17.83 mmol) in EtOH (5.5 mL) was added ammonium acetate (2.74 g, 35.58 mmol) and malonic acid (1.85 g, 17.78 mmol). The reaction mixture was stirred was refluxed for 7 h. The precipitate formed was filtered and washed with boiling EtOH (3 × 10 mL) to give 2 (2.20 g, yield 72%) as a white solid. Mp 223-224 °C. IR (KBr): ν = 2954, 2152, 1532, 1403, 1101, 992, 925, 786 cm-1. 1H NMR (300 MHz, TFA-d): δ = 11.03 (br s, 3H, D2O exch., OH + NH2), 6.97-6.91 (m, 2H, 2-Hthiophene and 5-Hthiophene), 6.63-6.61 (m, 1H, 4-Hthiophene), 4.58-4.54 (m, 1H, 3-H), 2.92 (dd, 1H, J = 18.4, 9.6 Hz, 2-HH), 2.72 (dd, 1H, J = 18.4, 4.2 Hz, 2-HH) ppm. 13C NMR (75 MHz, TFA-d): δ = 175.01 (CO), 131.92 (C2thiophene), 126.76 (C4thiophene), 123.48 and 122.45 (C3thiophene and C5thiophene), 47.01 (CH), 34.12 (CH2) ppm. EIMS: m/z (%) = 172 (2) [M + 1]+, 171 (17) [M+], 112 (100) [M+ - CH2COOH], 111 (3), 110 (17), 85 (54), 84 (4), 83 (3) [M+ - C3H6NO2], 70 (5), 58 (13). Anal. calcd. for C7H9NO2S (171.21): C 49.10, H 5.30, N 8.18; found C 49.43, H 5.37, N 8.05.
References:
Prado-Prado, Francisco;García-Mera, Xerardo;Abeijón, Paula;Alonso, Nerea;Caama?o, Olga;Yá?ez, Matilde;Gárate, Teresa;Mezo, Mercedes;González-Warleta, Marta;Mui?o, Laura;Ubeira, Florencio M.;González-Díaz, Humberto [European Journal of Medicinal Chemistry,2011,vol. 46,# 4,p. 1074 - 1094] Location in patent:experimental part
498-62-4
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94333-62-7
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498-62-4
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631-61-8
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94333-62-7
22 suppliers
$45.00/50mg
498-62-4
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$5.00/1g
94333-62-7
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1195-52-4
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