[(S)-1-((6S,12R)-6-Benzyl-1-methyl-5,8,11-trioxo-1,4,7,10-tetraaza-cyclotridec-12-ylcarbamoyl)-2-(4-benzyloxy-phenyl)-ethyl]-carbamic acid benzyl ester

Base Information

• Chemical Name: [(S)-1-((6S,12R)-6-Benzyl-1-methyl-5,8,11-trioxo-1,4,7,10-tetraaza-cyclotridec-12-ylcarbamoyl)-2-(4-benzyloxy-phenyl)-ethyl]-carbamic acid benzyl ester
• CAS No.: 210818-43-2
• Molecular Formula: C₄₁H₄₆N₆O₇
• Molecular Weight: 734.852

Synonyms:[(S)-1-((6S,12R)-6-Benzyl-1-methyl-5,8,11-trioxo-1,4,7,10-tetraaza-cyclotridec-12-ylcarbamoyl)-2-(4-benzyloxy-phenyl)-ethyl]-carbamic acid benzyl ester

Chemical Property of [(S)-1-((6S,12R)-6-Benzyl-1-methyl-5,8,11-trioxo-1,4,7,10-tetraaza-cyclotridec-12-ylcarbamoyl)-2-(4-benzyloxy-phenyl)-ethyl]-carbamic acid benzyl ester

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Technology Process of [(S)-1-((6S,12R)-6-Benzyl-1-methyl-5,8,11-trioxo-1,4,7,10-tetraaza-cyclotridec-12-ylcarbamoyl)-2-(4-benzyloxy-phenyl)-ethyl]-carbamic acid benzyl ester

There total 7 articles about [(S)-1-((6S,12R)-6-Benzyl-1-methyl-5,8,11-trioxo-1,4,7,10-tetraaza-cyclotridec-12-ylcarbamoyl)-2-(4-benzyloxy-phenyl)-ethyl]-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: 49.0%

{(R)-3-{[2-((S)-2-Amino-3-phenyl-propionylamino)-ethyl]-methyl-amino}-2-[(S)-2-benzyloxycarbonylamino-3-(4-benzyloxy-phenyl)-propionylamino]-propionylamino}-acetic acid → [(S)-1-((6S,12R)-6-Benzyl-1-methyl-5,8,11-trioxo-1,4,7,10-tetraaza-cyclotridec-12-ylcarbamoyl)-2-(4-benzyloxy-phenyl)-ethyl]-carbamic acid benzyl ester (210818-43-2)

Guidance literature:

With 1-hydroxy-7-aza-benzotriazole; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; In dichloromethane; N,N-dimethyl-formamide; for 168h;

DOI:10.1021/jm970861r

Reference yield:

N-benzyloxycarbonyl-O-benzyl-L-tyrosine (86827-18-1,92455-53-3,16677-29-5) → [(S)-1-((6S,12R)-6-Benzyl-1-methyl-5,8,11-trioxo-1,4,7,10-tetraaza-cyclotridec-12-ylcarbamoyl)-2-(4-benzyloxy-phenyl)-ethyl]-carbamic acid benzyl ester (210818-43-2)

Guidance literature:

Multi-step reaction with 3 steps

1: DIEA, BOP / dimethylformamide / 48 h

2: TFA / CH₂Cl₂ / 1 h

3: 49 percent / HOAt, DIEA, EDC / dimethylformamide; CH₂Cl₂ / 168 h

With 1-hydroxy-7-aza-benzotriazole; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; In dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm970861r

Reference yield:

N-butoxycarbonyl-L-phenylalanine anhydride (142955-51-9) → [(S)-1-((6S,12R)-6-Benzyl-1-methyl-5,8,11-trioxo-1,4,7,10-tetraaza-cyclotridec-12-ylcarbamoyl)-2-(4-benzyloxy-phenyl)-ethyl]-carbamic acid benzyl ester (210818-43-2)

Guidance literature:

Multi-step reaction with 6 steps

1: 50 percent / CH₂Cl₂ / 1.5 h / Ambient temperature

2: 1.) Cs₂CO₃, 2.) BOP / 1.) DMF, RT, 24 h, 2.) DMF, RT, 52 h

3: H₂ / 10percent Pd/C / ethanol / 19 h

4: DIEA, BOP / dimethylformamide / 48 h

5: TFA / CH₂Cl₂ / 1 h

6: 49 percent / HOAt, DIEA, EDC / dimethylformamide; CH₂Cl₂ / 168 h

With 1-hydroxy-7-aza-benzotriazole; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; caesium carbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; palladium on activated charcoal; In ethanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm970861r

upstream raw materials:

N-benzyloxycarbonyl-O-benzyl-L-tyrosine

N-butoxycarbonyl-L-phenylalanine anhydride

Boc-L-Phe-NH(CH₂)2NHMe

((R)-2-Benzyloxycarbonylamino-3-{[2-((S)-2-tert-butoxycarbonylamino-3-phenyl-propionylamino)-ethyl]-methyl-amino}-propionylamino)-acetic acid tert-butyl ester

Downstream raw materials:

(S)-2-Amino-N-((6S,12R)-6-benzyl-1-methyl-5,8,11-trioxo-1,4,7,10-tetraaza-cyclotridec-12-yl)-3-(4-hydroxy-phenyl)-propionamide

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