2-(Acetylamino)-2-[2-(4-octylphenyl)-2-oxoethyl]-propanedioic acid 1,3-diethyl ester synthesis
- Product Name:2-(Acetylamino)-2-[2-(4-octylphenyl)-2-oxoethyl]-propanedioic acid 1,3-diethyl ester
- CAS Number:268557-49-9
- Molecular formula:C25H37NO6
- Molecular Weight:447.56
Yield:268557-49-9 94%
Reaction Conditions:
with caesium carbonate in acetonitrile; for 4 h;Reflux;
Steps:
12.2 12.2 Diethyl 2-acetamido-2-(2-(4-octylphenyl)-2-oxoethyl)malonate
12.2
Diethyl 2-acetamido-2-(2-(4-octylphenyl)-2-oxoethyl)malonate
Bromo derivative 68 (8.90 g, 19.7 mmol, purity: 69% (GC), 1.3 eq.), diethyl 2-acetamidomalonate 1 (3.21 g, 14.8 mmol), obtained as in example 1.1, and caesium carbonate (5.15 g, 15.8 mmol, 1.1 eq) were suspended in acetonitrile (125 mL) and heated to reflux for 4 h.
After cooling to r.t. the mixture was adsorbed on silica gel (15 g) and purified by column chromatography (10.5*8 cm, cyclohexane/ethyl acetate, 4:1→2:1).
The product was isolated as pale yellow oil. Yield: 5.87 g (94%).
1H-NMR (400 MHz, CDCl3) δ [ppm]: 0.87 (t, 3JH,H=6.7 Hz, 3H, 19-CH3), 1.24 (t, 3JH,H=7.1 Hz, 6H, 23-CH3, 25-CH3), 1.26-1.33 (m, 10H, 14-CH2 to 18-CH2), 1.61 (m, 2H, 13-CH2), 1.97 (s, 3H, 21-CH3), 2.66 (m, 2H, 12-CH2), 4.25 (s, 2H, 4-CH2), 4.27 (2 q, 3JH,H=7.1 Hz, 4H, 22-CH2, 24-CH2), 7.15 (s, 1H, 2-NH), 7.26, 7.88 (m, 2H, 7-CH, 11-CH or 8-CH, 10-CH), 7.88 (m, 2H, 7-CH, 11-CH or 8-CH, 10-CH).
13C-NMR (101 MHz, CDCl3) δ [ppm]: 13.9 (q, C-23, C-25), 14.1 (q, C-19), 22.7 (t, C-18), 22.9 (q, C-21), 29.2, 29.4, 31.1 (t, C-13 to C-16), 31.9 (t, C-17), 36.0 (t, C-12), 42.2 (t, C-4), 62.8 (t, C-22, C-24), 64.0 (s, C-2), 128.4, 128.7 (d, C-7, C-8, C-10, C-11), 133.8, 149.6 (s, C-9, C-6), 167.4 (s, C-1, C-3), 169.4 (s, C-20), 196.5 (s, C-5).
Exact mass (ESI+): C25H37NO6+H+: calcd. 448.2694, found 448.2689; C25H37NO6+Na+: calcd. 470.2513, found 470.2505; (C25H37NO6)2+Na+: calcd. 917.5134, found 917.5132.
References:
US2014/170067,2014,A1 Location in patent:Paragraph 0486; 0487; 0488; 0489
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