ChemicalBook CAS DataBase List N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine

N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine synthesis

11synthesis methods

Product Name:N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine
CAS Number:82717-96-2
Molecular formula:C15H21NO4
Molecular Weight:279.34

Benzenebutanoic acid, α-[[(1S)-1-methyl-2-oxo-2-(phenylmethoxy)ethyl]amino]-γ-oxo-, ethyl ester, (αS)-

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N-[(S)-(+)-1-(Ethoxycarbonyl)-3-phenylpropyl]-L-alanine

82717-96-2
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Yield:82717-96-2 96%

Reaction Conditions:

with hydrogenchloride;palladium 10% on activated carbon;hydrogen;N,N-diphenylthiourea in 1,4-dioxane;isopropyl alcohol under 2250.23 Torr;Autoclave;Reagent/catalyst;Solvent;

Steps:

10
Hydrogenation reaction:To the autoclave (76.7 g, 0.2 mol of the above addition product)N-[1-(S)-ethoxycarbonyl-2-benzoylethyl]-L-alanine benzyl ester and isopropanol (2L),Hydrogen chloride in 1,4-dioxane solution (4 mol/L, 0.2 mol) andN,N'-diphenylthiourea (0.11 mmol);Adding 10% by weight of palladium carbon (Pd content is 0.1% by weight);Nitrogen replacement,After hydrogen replacement,Pressurized to 0.3 MPa,Insulation reaction,The reaction is followed by TLC or HPLC until the above-mentioned addition product disappears.filter,After the filtrate is decolorized with activated carbon,Concentrated under reduced pressure to remove most of the organic solvent.The remaining 3 to 4 vol,To this was added methyl tertiary tert-butyl ether 10 vol.Cool down to 0 ~ 10 ° C, pulping and purification,filter,After collecting the filter cake, it is 54.2g of ECPPA pure product.The yield is 96% by weight;Purity >98%,Ee>99%.

References:

Kailaiying Pharmaceutical Group (Tianjin) Co., Ltd.;Lu Jiangping;Li Jiuyuan;Li Changfeng CN108147973, 2018, A Location in patent:Paragraph 0067; 0074; 0078; 0082; 0086; 0090; 0094; 0098

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