[4-((3S,8S,9S,12S)-3-Benzyl-4,10,13-trioxo-8-phenyl-2,5,11,14-tetraaza-tricyclo[14.3.1.0^5,9]icosa-1⁽²⁰⁾,16,18-trien-12-yl)-butyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [4-((3S,8S,9S,12S)-3-Benzyl-4,10,13-trioxo-8-phenyl-2,5,11,14-tetraaza-tricyclo[14.3.1.0^5,9]icosa-1⁽²⁰⁾,16,18-trien-12-yl)-butyl]-carbamic acid benzyl ester
• CAS No.: 221526-03-0
• Molecular Formula: C₄₁H₄₅N₅O₅
• Molecular Weight: 687.839

Synonyms:[4-((3S,8S,9S,12S)-3-Benzyl-4,10,13-trioxo-8-phenyl-2,5,11,14-tetraaza-tricyclo[14.3.1.0^5,9]icosa-1⁽²⁰⁾,16,18-trien-12-yl)-butyl]-carbamic acid benzyl ester

Chemical Property of [4-((3S,8S,9S,12S)-3-Benzyl-4,10,13-trioxo-8-phenyl-2,5,11,14-tetraaza-tricyclo[14.3.1.0^5,9]icosa-1⁽²⁰⁾,16,18-trien-12-yl)-butyl]-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

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Technology Process of [4-((3S,8S,9S,12S)-3-Benzyl-4,10,13-trioxo-8-phenyl-2,5,11,14-tetraaza-tricyclo[14.3.1.0^5,9]icosa-1⁽²⁰⁾,16,18-trien-12-yl)-butyl]-carbamic acid benzyl ester

There total 11 articles about [4-((3S,8S,9S,12S)-3-Benzyl-4,10,13-trioxo-8-phenyl-2,5,11,14-tetraaza-tricyclo[14.3.1.0^5,9]icosa-1⁽²⁰⁾,16,18-trien-12-yl)-butyl]-carbamic acid benzyl 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: 30.0%

(S)-2-({(2S,3S)-1-[(S)-2-(3-Aminomethyl-phenylamino)-3-phenyl-propionyl]-3-phenyl-pyrrolidine-2-carbonyl}-amino)-6-benzyloxycarbonylamino-hexanoic acid; compound with trifluoro-acetic acid → [4-((3S,8S,9S,12S)-3-Benzyl-4,10,13-trioxo-8-phenyl-2,5,11,14-tetraaza-tricyclo[14.3.1.05,9]icosa-1(20),16,18-trien-12-yl)-butyl]-carbamic acid benzyl ester (221526-03-0)

Guidance literature:

With TEA; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; In acetonitrile; 1.) 0 deg C, 1 h, 2.) r.t., 3 h;

DOI:10.1055/s-1999-2578

Reference yield:

(S)-methyl 2-amino-6-(benzyloxycarbonylamino)hexanoate (24498-31-5) → [4-((3S,8S,9S,12S)-3-Benzyl-4,10,13-trioxo-8-phenyl-2,5,11,14-tetraaza-tricyclo[14.3.1.05,9]icosa-1(20),16,18-trien-12-yl)-butyl]-carbamic acid benzyl ester (221526-03-0)

Guidance literature:

Multi-step reaction with 6 steps

1: 35 percent / HOBt, EDCI, TEA / CH₂Cl₂; tetrahydrofuran / 12 h / Ambient temperature

2: 93 percent / CF₃COOH / CHCl₃ / 12 h / Ambient temperature

3: 80 percent / BOP, DIEA / acetonitrile / 12 h / Ambient temperature

4: 100 percent / NaOH, H₂O / tetrahydrofuran / 12 h / Ambient temperature

5: 81 percent / CHCl₃ / 12 h / Ambient temperature

6: 30 percent / BOP, TEA / acetonitrile / 1.) 0 deg C, 1 h, 2.) r.t., 3 h

With sodium hydroxide; TEA; water; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; chloroform; acetonitrile;

DOI:10.1055/s-1999-2578

Reference yield:

(2S,3S)-3-phenyl-pyrrolidine-2-carboxylic acid (118758-49-9) → [4-((3S,8S,9S,12S)-3-Benzyl-4,10,13-trioxo-8-phenyl-2,5,11,14-tetraaza-tricyclo[14.3.1.05,9]icosa-1(20),16,18-trien-12-yl)-butyl]-carbamic acid benzyl ester (221526-03-0)

Guidance literature:

Multi-step reaction with 7 steps

1: 87 percent / Na₂CO₃ / dioxane / 12 h / Ambient temperature

2: 35 percent / HOBt, EDCI, TEA / CH₂Cl₂; tetrahydrofuran / 12 h / Ambient temperature

3: 93 percent / CF₃COOH / CHCl₃ / 12 h / Ambient temperature

4: 80 percent / BOP, DIEA / acetonitrile / 12 h / Ambient temperature

5: 100 percent / NaOH, H₂O / tetrahydrofuran / 12 h / Ambient temperature

6: 81 percent / CHCl₃ / 12 h / Ambient temperature

7: 30 percent / BOP, TEA / acetonitrile / 1.) 0 deg C, 1 h, 2.) r.t., 3 h

With sodium hydroxide; TEA; water; sodium carbonate; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; dichloromethane; chloroform; acetonitrile;

DOI:10.1055/s-1999-2578

upstream raw materials:

(S)-methyl 2-amino-6-(benzyloxycarbonylamino)hexanoate

(2S,3S)-3-phenyl-pyrrolidine-2-carboxylic acid

3-tert-butoxycarbonylaminomethylaniline

(S)-6-Benzyloxycarbonylamino-2-[((2S,3S)-1-{(S)-2-[3-(tert-butoxycarbonylamino-methyl)-phenylamino]-3-phenyl-propionyl}-3-phenyl-pyrrolidine-2-carbonyl)-amino]-hexanoic acid

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