{[2-(2-tert-butoxycarbonylamino-3-phenyl-propionyl)-isoxazolidine-3-carbonyl]-amino}-acetic acid ethyl ester

Base Information

• Chemical Name: {[2-(2-tert-butoxycarbonylamino-3-phenyl-propionyl)-isoxazolidine-3-carbonyl]-amino}-acetic acid ethyl ester
• CAS No.: 221019-72-3
• Molecular Formula: C₂₂H₃₁N₃O₇
• Molecular Weight: 449.504

Synonyms:{[2-(2-tert-butoxycarbonylamino-3-phenyl-propionyl)-isoxazolidine-3-carbonyl]-amino}-acetic acid ethyl ester

Chemical Property of {[2-(2-tert-butoxycarbonylamino-3-phenyl-propionyl)-isoxazolidine-3-carbonyl]-amino}-acetic acid ethyl ester

Chemical Property:

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Technology Process of {[2-(2-tert-butoxycarbonylamino-3-phenyl-propionyl)-isoxazolidine-3-carbonyl]-amino}-acetic acid ethyl ester

There total 2 articles about {[2-(2-tert-butoxycarbonylamino-3-phenyl-propionyl)-isoxazolidine-3-carbonyl]-amino}-acetic 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: 65.0%

N-tert-butoxycarbonyl-L-phenylalanine (13734-34-4) + [(isoxazolidine-3-carbonyl)-amino]-acetic acid ethyl ester (221019-71-2) → {[2-(2-tert-butoxycarbonylamino-3-phenyl-propionyl)-isoxazolidine-3-carbonyl]-amino}-acetic acid ethyl ester (221019-72-3)

Guidance literature:

With N-ethylmorpholine;; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran;

DOI:10.1021/ja981193h

Reference yield:

({2-[(3aR,6R,6aR)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-isoxazolidine-3-carbonyl}-amino)-acetic acid ethyl ester (221019-70-1) → {[2-(2-tert-butoxycarbonylamino-3-phenyl-propionyl)-isoxazolidine-3-carbonyl]-amino}-acetic acid ethyl ester (221019-72-3)

Guidance literature:

Multi-step reaction with 2 steps

1: 73 percent / 37 percent aq. HCl / ethanol

2: 65 percent / DCC, HOBt, N-ethylmorpholine / tetrahydrofuran

With N-ethylmorpholine;; hydrogenchloride; benzotriazol-1-ol; dicyclohexyl-carbodiimide; In tetrahydrofuran; ethanol;

DOI:10.1021/ja981193h

Reference yield:

{[2-(2-tert-butoxycarbonylamino-3-phenyl-propionyl)-isoxazolidine-3-carbonyl]-amino}-acetic acid ethyl ester (221019-72-3) → {[(R)-2-((S)-2-Amino-3-phenyl-propionyl)-isoxazolidine-3-carbonyl]-amino}-acetic acid ethyl ester + {[(S)-2-((S)-2-Amino-3-phenyl-propionyl)-isoxazolidine-3-carbonyl]-amino}-acetic acid ethyl ester (221019-73-4)

Guidance literature:

With trifluoroacetic acid; In dichloromethane; at 0 ℃;

DOI:10.1021/ja981193h

upstream raw materials:

N-tert-butoxycarbonyl-L-phenylalanine

[(isoxazolidine-3-carbonyl)-amino]-acetic acid ethyl ester

({2-[(3aR,6R,6aR)-6-((R)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-2,2-dimethyl-tetrahydro-furo[3,4-d][1,3]dioxol-4-yl]-isoxazolidine-3-carbonyl}-amino)-acetic acid ethyl ester

Downstream raw materials:

{[(S)-2-((S)-2-Amino-3-phenyl-propionyl)-isoxazolidine-3-carbonyl]-amino}-acetic acid ethyl ester

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