L-amino acid-6-gliotoxin ester trifluoroacetate and preparation method thereof
A technology of ester trifluoroacetate and gliotoxin, which is applied in the field of L-amino acid-6-gliotoxin ester trifluoroacetate compounds and their preparation, and can solve the problems of poor stability, severe toxic side effects, and restricted applications and development issues, to achieve the effect of expanding the structure type and good application prospects
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Embodiment 1
[0028]
[0029] Weigh 200mg of gliotoxin and dissolve it in 4mL of dichloromethane, stir at room temperature and add 1.1eq of N-Boc-L-sarcosine, 1eq of DCC and 0.1eq of DMAP, and perform TLC monitoring every 30min during the reaction , After 1.5-2h, the reaction is complete. Add 50mL of dichloromethane to the reaction system for dilution, and dilute the reaction system with saturated NH 4 The Cl solution was washed three times, and the aqueous phase was extracted once with dichloromethane. The organic phases were combined, washed three times with saturated NaCl solution, dried over anhydrous magnesium sulfate for 12 h, the organic phase was concentrated to obtain a crude extract, which was separated and purified by column chromatography to obtain a light yellow solid. Dissolve the above product in dichloromethane, add 300 μL trifluoroacetic acid under ice bath and stir, monitor by TLC every 30 minutes during the reaction, after 2-3 hours the reaction is complete, remove th...
Embodiment 2
[0031]
[0032] N-Boc-L-sarcosine was replaced by N-Boc-methyl-L-alanine, and other operations were the same as in Example 1 to obtain light yellow solid 3b with a yield of 65%, m.p.: 125.9-126.8°C; IR (KBr,cm -1 ):3429,1761,1685,1420,1383,1202,1062,798,722,703,672. 1 H NMR (400MHz, DMSO-d 6 )δ9.33(s,2H),6.06(dt,J=5.8,3.1Hz,1H),5.98(ddd,J=8.1,4.8,2.7Hz,1H),5.65(d,J=9.8Hz,1H ),5.18(d,J=12.7Hz,1H),5.08(d,J=12.7Hz,1H),4.86(d,J=13.1Hz,1H),4.56(d,J=13.1Hz,1H), 4.25(q,J=7.1Hz,1H),3.23(s,1H),3.18(s,1H),3.10(s,3H),2.62(s,3H),1.67(ddq,J=39.4,8.2, 3.9Hz, 1H), 1.48(d, J=7.2Hz, 3H). 13 C NMR (100MHz, DMSO-d 6 )δ168.17, 164.92, 163.06, 158.13, 132.21, 129.42, 123.66, 119.08, 118.09, 75.79, 75.32, 72.63, 69.45, 61.04, 54.92, 35.71, 30.43, 28.03, 13.63 17 h 22 N 3 o 5 S 2 [M-CF 3 COO - ] + :412.0995, found 412.1100.
Embodiment 3
[0034]
[0035] N-Boc-L-sarcosine was replaced by N-Boc-L-2-aminobutyric acid, and other operations were the same as in Example 1 to obtain light yellow solid 3c with a yield of 48%, m.p.: 121.6-122.5°C; IR( KBr,cm -1 ):3433,2928,1762,1685,1414,1379,1356,1203,1137,1061,835,799,722. 1 H NMR (400MHz, DMSO-d 6 )δ8.52(s,3H),5.98(dd,J=5.1,2.8Hz,1H),5.90(ddd,J=9.7,5.0,2.8Hz,1H),5.58(d,J=9.8Hz,1H ),5.41(d,J=18.3Hz,1H),5.12(d,J=12.8Hz,1H),4.99(d,J=12.7Hz,1H),4.79(d,J=13.1Hz,1H), 4.49(dd,J=13.0,2.8Hz,1H),3.61-3.54(m,1H),3.16(d,J=1.7Hz,1H),3.11(d,J=1.6Hz,1H),3.03(s ,3H),1.84–1.76(m,2H),0.91(t,J=7.5Hz,3H). 13 C NMR (100MHz, DMSO-d 6 )δ168.32, 164.91, 163.05, 158.12, 132.27, 129.46, 123.63, 119.04, 114.97, 75.81, 75.31, 72.62, 69.48, 61.01, 52.89, 35.73, c28.04, 23.33, 8.9ld.ESI 17 h 22 N 3 o 5 S 2 [M-CF 3 COO - ] + :412.0995, found 412.1001.
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