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Imidaprilat Benzyl Ester, (Carbonylimidazolidine)tert-butyl Ester synthesis

11synthesis methods
4-Imidazolidinecarboxylic acid, 1-methyl-3-[(2R)-2-[[(4-methylphenyl)sulfonyl]oxy]-1-oxopropyl]-2-oxo-, 1,1-dimethylethyl ester, (4S)-

130368-70-6
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Benzenebutanoic acid, α-amino-, phenylmethyl ester, (αS)-

83080-02-8
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Imidaprilat Benzyl Ester, (Carbonylimidazolidine)tert-butyl Ester

89460-20-8
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Yield:89460-20-8 82.3%

Steps:

5.1 EXAMPLE 5

(1) t-Butyl (4S)-1-methyl-3-[(2R)-2-(p-toluenesulfonyloxy)propionyl]-2-oxoimidazolidine-4-carboxylate (1 g) obtained in Example 1 - (1) and benzyl (2S)-2-amino-4-phenylbutyrate (1.55 g) were treated similarly as in Example 1 - (2) to give t-butyl (4S)-1-methyl-3-{(2S)-2-[N-((1S)-1-benzyloxycarbonyl-3-phenyl-propyl)amino]propionyl}-2-oxoimidazolidine-4-carboxylate (1.01 g) as colorless syrup. Yield: 82.3%. Maleic acid salt of this product: m.p.: 108°-112° C. [α]D25: -57.4° (C=1, ethanol).

References:

US5013845,1991,A