Trans-N-Boc-2-(4-chlorophenyl)-3-(isopropylamino) acrylic acid synthesis
- Product Name:Trans-N-Boc-2-(4-chlorophenyl)-3-(isopropylamino) acrylic acid
- CAS Number:1489004-27-4
- Molecular formula:C17H22ClNO4
- Molecular Weight:339.81
amino]methylene]-, ethyl ester, (αE)-](/CAS/20210305/GIF/1489004-24-1.gif)
1489004-24-1
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1489004-27-4
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Yield:1489004-27-4 90.5%
Reaction Conditions:
with water;sodium hydroxide in ethanol at 20 - 45; for 2.5 h;Large scale;
Steps:
1
(E)-3-(^r/-butoxycarbonyl(isopropyI)amino)-2-(4-chlorophenyI)acrylic acid. (￡)- ethyl 3-((r/-butoxycarbonylXisopropyl)amino)-2-(4-chlorophenyl)acrylate ( 133.5 kg, 362.9 mol) was added into a mixture of H20 (252 L), NaOH (58.25 kg, 1456 mol) and EtOH (383.5 L) stirred at room temperature. The mixture was warmed to 40-45 C for 2.5 h until a clear slution was formed. The mixture was concentrated to a minimum working volume maintoaining the temperature below 50 C. The mixture was then cooled to 10-25 C and a solution of HC1 was added (842 L of 2N HC1 and 1 1 L of 35% HC1) until a final pH = 2-4 was obtained. The aqueous layer was separated and the organic layer was washed with 25% aqueous NaCl (810 L). ^-Heptane was added while distilling to form a suspension. The product was collected and washed with -heptane and dried at 40^15 °C for -10 h to afford 1 10.7 kg (90.5% yield) of (￡)- 3-(tert-butoxycarbonyl(isopropyl)amino)-2-(4-chlorophenyl)acrylic acid having 99.9 A% purity by HPLC. E-configuration was confirmed using single crystal x-ray analysis (See Figure 1 ).
References:
WO2013/173779,2013,A1 Location in patent:Paragraph 0087
24424-99-5
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1489004-27-4
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33691-09-7
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1489004-27-4
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