{2S-[2α,3β(S)]}-3-{[(3-Phenyl-1-{[(5-hydroxypentyl)amino]carbonyl}propyl)amino]carbonyl}oxirane carboxylic acid ethyl ester

Base Information

• Chemical Name: {2S-[2α,3β(S)]}-3-{[(3-Phenyl-1-{[(5-hydroxypentyl)amino]carbonyl}propyl)amino]carbonyl}oxirane carboxylic acid ethyl ester
• CAS No.: 245660-32-6
• Molecular Formula: C₂₁H₃₀N₂O₆
• Molecular Weight: 406.479

Synonyms:{2S-[2α,3β(S)]}-3-{[(3-Phenyl-1-{[(5-hydroxypentyl)amino]carbonyl}propyl)amino]carbonyl}oxirane carboxylic acid ethyl ester

Chemical Property of {2S-[2α,3β(S)]}-3-{[(3-Phenyl-1-{[(5-hydroxypentyl)amino]carbonyl}propyl)amino]carbonyl}oxirane carboxylic acid ethyl ester

Chemical Property:

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Technology Process of {2S-[2α,3β(S)]}-3-{[(3-Phenyl-1-{[(5-hydroxypentyl)amino]carbonyl}propyl)amino]carbonyl}oxirane carboxylic acid ethyl ester

There total 5 articles about {2S-[2α,3β(S)]}-3-{[(3-Phenyl-1-{[(5-hydroxypentyl)amino]carbonyl}propyl)amino]carbonyl}oxirane carboxylic acid ethyl ester which guide to synthetic route it. The literature collected by LookChem mainly comes from the sharing of users and the free literature resources found by Internet computing technology. We keep the original model of the professional version of literature to make it easier and faster for users to retrieve and use. At the same time, we analyze and calculate the most feasible synthesis route with the highest yield for your reference as below:

synthetic route:

Reference yield: 95.0%

{2S-[2α,3β(S)]}-3-{[(3-Phenyl-1-{[(5-t-butyldimethylsilanoxylpentyl)amino]carbonyl}propyl)amino]carbonyl}oxirane carboxylic acid ethyl ester (245660-28-0) → {2S-[2α,3β(S)]}-3-{[(3-Phenyl-1-{[(5-hydroxypentyl)amino]carbonyl}propyl)amino]carbonyl}oxirane carboxylic acid ethyl ester (245660-32-6)

Guidance literature:

With hydrogen fluoride; water; In dichloromethane; acetonitrile; at 23 ℃; for 0.25h;

DOI:10.1055/s-1999-3648

Reference yield:

ethyl (2S,3S)-2,3-epoxysuccinate (63734-73-6,66647-16-3,68521-71-1,89886-73-7,93061-20-2,149884-11-7) → {2S-[2α,3β(S)]}-3-{[(3-Phenyl-1-{[(5-hydroxypentyl)amino]carbonyl}propyl)amino]carbonyl}oxirane carboxylic acid ethyl ester (245660-32-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 77 percent / EDC; HOBT; N-methylmorpholine / CHCl₃ / 10 h / 0 - 23 °C

2: 95 percent / H₂ / 10 percent Pd/C / methanol; ethyl acetate / 0.17 h / 2068.59 Torr

3: 66 percent / EDC; HOBT; N-methylmorpholine / CHCl₃ / 10 h / 0 - 23 °C

4: 95 percent / H₂O; HF / acetonitrile; CH₂Cl₂ / 0.25 h / 23 °C

With 4-methyl-morpholine; hydrogen fluoride; water; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; In methanol; dichloromethane; chloroform; ethyl acetate; acetonitrile; 1: Acylation / 2: Hydrogenolysis / 3: Acylation / 4: Hydrolysis;

DOI:10.1055/s-1999-3648

Reference yield:

p-tolylsulfonic caid salt of L-homophenylalanine benzyl ester (117560-24-4) → {2S-[2α,3β(S)]}-3-{[(3-Phenyl-1-{[(5-hydroxypentyl)amino]carbonyl}propyl)amino]carbonyl}oxirane carboxylic acid ethyl ester (245660-32-6)

Guidance literature:

Multi-step reaction with 4 steps

1: 77 percent / EDC; HOBT; N-methylmorpholine / CHCl₃ / 10 h / 0 - 23 °C

2: 95 percent / H₂ / 10 percent Pd/C / methanol; ethyl acetate / 0.17 h / 2068.59 Torr

3: 66 percent / EDC; HOBT; N-methylmorpholine / CHCl₃ / 10 h / 0 - 23 °C

4: 95 percent / H₂O; HF / acetonitrile; CH₂Cl₂ / 0.25 h / 23 °C

With 4-methyl-morpholine; hydrogen fluoride; water; hydrogen; benzotriazol-1-ol; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; palladium on activated charcoal; In methanol; dichloromethane; chloroform; ethyl acetate; acetonitrile; 1: Acylation / 2: Hydrogenolysis / 3: Acylation / 4: Hydrolysis;

DOI:10.1055/s-1999-3648

upstream raw materials:

{2S-[2α,3β(S)]}-3-{[(3-Phenyl-1-{[(5-t-butyldimethylsilanoxylpentyl)amino]carbonyl}propyl)amino]carbonyl}oxirane carboxylic acid ethyl ester

ethyl (2S,3S)-2,3-epoxysuccinate

p-tolylsulfonic caid salt of L-homophenylalanine benzyl ester

{2S-[2α,3β(S)]}-3({[3-Phenyl-1-(carboxyl)propyl]amino}carbonyl)oxirane carboxylic acid ethyl ester

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