(S)-benzyl 1-(4-phenyl-1H-iMidazol-2-yl)ethylcarbaMate synthesis

4synthesis methods

Product Name:(S)-benzyl 1-(4-phenyl-1H-iMidazol-2-yl)ethylcarbaMate
CAS Number:864825-21-8
Molecular formula:C19H19N3O2
Molecular Weight:321.37

(S)-benzyl 1-oxo-1-(2-oxo-2-phenylethylaMino)propan-2-ylcarbaMate

864825-19-4
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(S)-benzyl 1-(4-phenyl-1H-iMidazol-2-yl)ethylcarbaMate

864825-21-8
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Yield:864825-21-8 95%

Reaction Conditions:

with ammonium acetate;acetic acid in xylene; for 7 h;Heating / reflux;

Steps:

1.B 2-Amino-3-(4-hydroxy-2,6-dimethyl-phenyl)-N-isopropyl-N-[1-(4-phenyl-1H-imidazol-2-yl)-ethyl]-propionamide

B. [1-(4-Phenyl-1H-imidazol-2-yl)-ethyl]-carbamic acid benzyl ester. To a suspension of [1-(2-oxo-2-phenyl-ethylcarbamoyl)-ethyl]-carbamic acid benzyl ester (2.60 g, 7.64 mmol) in xylene (60 mL) was added NH₄OAc (10.3 g, 134 mmol) and HOAc (5 mL). The resulting mixture was heated at reflux for 7 h. After being cooled to room temperature, brine was added and the mixture was separated. The aqueous phase was extracted with EtOAc, and the combined organic phases were dried over Na₂SO₄ overnight. After filtration and concentration, the residue was purified by column chromatography on silica gel (eluent, EtOAc:hexane-1:1) to give the title compound (2.33 g, 95%). ¹H NMR (300 MHz, CDCl₃): δ 1.65 (3H, d), 5.06 (1H, m), 5.14 (2H, q), 5.94 (1H, d), 7.32 (10H, m), 7.59 (2H, d). MS(ES⁺): 322.2 (100%).

References:

US2005/203143,2005,A1 Location in patent:Page/Page column 32

1142-20-7 Synthesis

1142-20-7
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References

5468-37-1 Synthesis

5468-37-1
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$17.00/5G

864825-21-8
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References

6530-41-2 Synthesis

L-Alanine, N-[(phenylmethoxy)carbonyl]-, 2-oxo-2-phenylethyl ester

6530-41-2
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References