N-4-Benzyloxyphenyl α-Benzilidene Isobutyrylacetamide synthesis

4synthesis methods

Product Name:N-4-Benzyloxyphenyl α-Benzilidene Isobutyrylacetamide
CAS Number:163217-66-1
Molecular formula:C26H25NO3
Molecular Weight:399.48

100-52-7 Synthesis

100-52-7
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265989-30-8
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N-4-Benzyloxyphenyl α-Benzilidene Isobutyrylacetamide

163217-66-1
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Yield:163217-66-1 46.2%

Reaction Conditions:

with acetic acid;3-amino propanoic acid in hexanes; for 28 h;Heating / reflux;

Steps:

H.9.B

The reaction was run in a 1 L three necked round bottomed flask equipped with an electric motor-driven mechanical stirrer and an oil bath. The flask was fitted with a Dean- Stark trap and a condenser, and the entire apparatus was maintained under nitrogen. The flask EPO . . was charged with 4-Methyl-3-oxo-pentanoic acid (4-benzyloxy-phenyl)-amide (27 g, 86.7 mmol), benzaldehyde (9.02 g, 85 mmol), β-alanine (2.04 g, 23 mmol), hexanes (400 ml_), and glacial acetic acid (2.04 g, 33.9 mmol), and the contents were heated under reflux for 28h, resulting in slurry. The crude mixture was filtered and then the filtrate was dissolved in dichloromethane and washed with water (3 x 100 mL). The organic layer was dried over magnesium sulfate. The solvents were removed and the product was purified by flash chromatography (SiOa), eluting with EtOAc/Hexanes (0:100 to 50:50) to afford 2-Benzylidene-4-methyl-3-oxo-pentanoic acid (4-benzyloxy-phenyl)-amide as a yellowish brown solid (16 g, 46.2%); ¹HNMR (CDCI₃): δ 7.8-7.2(m, 12H), 7.1-6.9(m, 2H), 6.7-6.6(m, 1 H), 5.1 (s, 2H), 3.5-3.3(m, 1H), 1.2(d, 6H); MS (ESI) m/z 400 [M+H]⁺.

References:

WO2006/110918,2006,A1 Location in patent:Page/Page column 57; 58

6373-46-2 Synthesis

6373-46-2
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163217-66-1
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References

42558-54-3 Synthesis

42558-54-3
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163217-66-1
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References

563-80-4
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$18.00/25mL

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References