FUSARIC ACID synthesis
- Product Name:FUSARIC ACID
- CAS Number:536-69-6
- Molecular formula:C10H13NO2
- Molecular Weight:179.22
17072-93-4
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536-69-6
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Yield: 75%
Reaction Conditions:
with sodium hydroxide in tetrahydrofuran;water at 0 - 20; for 15 h;
Steps:
4.2.4. General synthetic procedure for compounds FA, 5a-m and 20
General procedure: Ester (FAE, 4a-m, 2a or 2b) (500 mg scale, 1 equiv.) was dissolvedin 6 ml THF at 0 °C in a 25 ml round-bottom flask. ThenNaOH(aq) (5 equiv.) was added dropwise and stirred for 15 h atroom temperature. After starting materials were consumed (byTLC), water (20 ml) was added. The reaction mixture was washedwith ethyl acetate (2 x 20 ml). The aqueous solution was acidified(pH 2-3) with 1 M HCl(aq) causing precipitation of a solid, whichwas filtered and dried under vacuum. Recrystallization in ethanolafford clean compound.4.2.4.1. Fusaric acid (FA). FAE (500 mg) gave FA (324 mg, 75%);slightly yellow solid; >99% purity after recrystallization fromethanol; mp 96.9-98.0 °C (reported 96-99 °C[30c]); 1H NMR(600 MHz, DMSO-d6):δ 8.46 (d, J = 2.2 Hz, 1H, H2), 8.16 (d,J= 8.1 Hz, 1H, H5), 7.76 (dd, J = 8.1, 2.2 Hz, 1H, H6), 2.74 (t, J = 7.7 Hz,2H, H10), 1.66 (m, 2H, H11), 1.4 (tq, J 7.7, 7.3 Hz, 2H, H12), 0.96 (t,J = 7.3 Hz, 3H, H13); 13C NMR (151 MHz, DMSO-d6) δ 164.2(C=O, C-7),148.2(C-2), 143.8(C-4), 143.5(C-1), 138.1(C-6),123.4(C-5), 32.9(C-11), 32.8(C-10), 22.2(C-12), 13.8(C-13); HRMS (ESI) m/z [M+H]+calcd for C10H14NO2+ 180.1025, found 180.1025. Data was in accordancewith those reported [19].
References:
Tung, Truong Thanh;Jakobsen, Tim Holm;Dao, Trong Tuan;Fuglsang, Anja Thoe;Givskov, Michael;Christensen, S?ren Br?gger;Nielsen, John [European Journal of Medicinal Chemistry,2017,vol. 126,p. 1011 - 1020]
17072-92-3
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1000210-73-0
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536-69-6
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536-69-6
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536-69-6
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