((4S,10S)-3,9,16,19,22-Pentaoxo-24-phenoxymethyl-2,8,15,18,21-pentaaza-tricyclo[21.3.1.0^4,8]heptacosa-1⁽²⁷⁾,23,25-trien-10-yl)-carbamic acid benzyl ester

Base Information

• Chemical Name: ((4S,10S)-3,9,16,19,22-Pentaoxo-24-phenoxymethyl-2,8,15,18,21-pentaaza-tricyclo[21.3.1.0^4,8]heptacosa-1⁽²⁷⁾,23,25-trien-10-yl)-carbamic acid benzyl ester
• CAS No.: 208587-15-9
• Molecular Formula: C₃₇H₄₂N₆O₈
• Molecular Weight: 698.776

Synonyms:((4S,10S)-3,9,16,19,22-Pentaoxo-24-phenoxymethyl-2,8,15,18,21-pentaaza-tricyclo[21.3.1.0^4,8]heptacosa-1⁽²⁷⁾,23,25-trien-10-yl)-carbamic acid benzyl ester

Chemical Property of ((4S,10S)-3,9,16,19,22-Pentaoxo-24-phenoxymethyl-2,8,15,18,21-pentaaza-tricyclo[21.3.1.0^4,8]heptacosa-1⁽²⁷⁾,23,25-trien-10-yl)-carbamic acid benzyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
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MSDS Files:

Useful:

Technology Process of ((4S,10S)-3,9,16,19,22-Pentaoxo-24-phenoxymethyl-2,8,15,18,21-pentaaza-tricyclo[21.3.1.0^4,8]heptacosa-1⁽²⁷⁾,23,25-trien-10-yl)-carbamic acid benzyl ester

There total 9 articles about ((4S,10S)-3,9,16,19,22-Pentaoxo-24-phenoxymethyl-2,8,15,18,21-pentaaza-tricyclo[21.3.1.0^4,8]heptacosa-1⁽²⁷⁾,23,25-trien-10-yl)-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:

2-phenoxymethyl-5-nitrobenzoic acid (129229-78-3) → ((4S,10S)-3,9,16,19,22-Pentaoxo-24-phenoxymethyl-2,8,15,18,21-pentaaza-tricyclo[21.3.1.04,8]heptacosa-1(27),23,25-trien-10-yl)-carbamic acid benzyl ester (208587-15-9)

Guidance literature:

Multi-step reaction with 8 steps

1: 1,) DCC, HOBt / 1.) CH₂Cl₂, THF, 0 deg C, 15 min, 2.) CH₂Cl₂, THF, a) 0 deg C, 1 h, b) RT, 24 h

2: H₂ / PtO₂ / dimethylformamide; methanol / 2 h / Ambient temperature

3: HOBt, DCC / CH₂Cl₂; tetrahydrofuran / a) 0 deg C, 2 h, b) RT, overnight

4: TFA / CH₂Cl₂ / 1.5 h / 0 °C

5: DCC, HOBt / CH₂Cl₂; tetrahydrofuran / a) 0 deg C, 2 h, b) RT, overnight

6: 70 percent / NH₂NH₂*H₂O / methanol / 24 h / Ambient temperature

7: TFA / CH₂Cl₂ / 2 h / 0 °C

8: 1.) isoamyl nitrite, 5.5 N HCl, 2.) diisopropylethylamine / 1.) DMF, THF, -40 deg C, 0.5 h, 2.) DMF, THF, 24 h

With hydrogenchloride; hydrogen; benzotriazol-1-ol; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; isopentyl nitrite; platinum(IV) oxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm970640l

Reference yield:

[2-(5-Nitro-2-phenoxymethyl-benzoylamino)-acetylamino]-acetic acid ethyl ester → ((4S,10S)-3,9,16,19,22-Pentaoxo-24-phenoxymethyl-2,8,15,18,21-pentaaza-tricyclo[21.3.1.04,8]heptacosa-1(27),23,25-trien-10-yl)-carbamic acid benzyl ester (208587-15-9)

Guidance literature:

Multi-step reaction with 7 steps

1: H₂ / PtO₂ / dimethylformamide; methanol / 2 h / Ambient temperature

2: HOBt, DCC / CH₂Cl₂; tetrahydrofuran / a) 0 deg C, 2 h, b) RT, overnight

3: TFA / CH₂Cl₂ / 1.5 h / 0 °C

4: DCC, HOBt / CH₂Cl₂; tetrahydrofuran / a) 0 deg C, 2 h, b) RT, overnight

5: 70 percent / NH₂NH₂*H₂O / methanol / 24 h / Ambient temperature

6: TFA / CH₂Cl₂ / 2 h / 0 °C

7: 1.) isoamyl nitrite, 5.5 N HCl, 2.) diisopropylethylamine / 1.) DMF, THF, -40 deg C, 0.5 h, 2.) DMF, THF, 24 h

With hydrogenchloride; hydrogen; benzotriazol-1-ol; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; isopentyl nitrite; platinum(IV) oxide; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide;

DOI:10.1021/jm970640l

Reference yield:

1-(tert-butoxycarbonyl)-L-proline (15761-39-4,59433-50-0) → ((4S,10S)-3,9,16,19,22-Pentaoxo-24-phenoxymethyl-2,8,15,18,21-pentaaza-tricyclo[21.3.1.04,8]heptacosa-1(27),23,25-trien-10-yl)-carbamic acid benzyl ester (208587-15-9)

Guidance literature:

Multi-step reaction with 6 steps

1: HOBt, DCC / CH₂Cl₂; tetrahydrofuran / a) 0 deg C, 2 h, b) RT, overnight

2: TFA / CH₂Cl₂ / 1.5 h / 0 °C

3: DCC, HOBt / CH₂Cl₂; tetrahydrofuran / a) 0 deg C, 2 h, b) RT, overnight

4: 70 percent / NH₂NH₂*H₂O / methanol / 24 h / Ambient temperature

5: TFA / CH₂Cl₂ / 2 h / 0 °C

6: 1.) isoamyl nitrite, 5.5 N HCl, 2.) diisopropylethylamine / 1.) DMF, THF, -40 deg C, 0.5 h, 2.) DMF, THF, 24 h

With hydrogenchloride; benzotriazol-1-ol; hydrazine hydrate; N-ethyl-N,N-diisopropylamine; dicyclohexyl-carbodiimide; trifluoroacetic acid; isopentyl nitrite; In tetrahydrofuran; methanol; dichloromethane;

DOI:10.1021/jm970640l

upstream raw materials:

1-(tert-butoxycarbonyl)-L-proline

2-phenoxymethyl-5-nitrobenzoic acid

(S)-2-(3-{[(Ethoxycarbonylmethyl-carbamoyl)-methyl]-carbamoyl}-4-phenoxymethyl-phenylcarbamoyl)-pyrrolidine-1-carboxylic acid tert-butyl ester

[2-(5-{[(S)-1-((S)-2-Benzyloxycarbonylamino-6-tert-butoxycarbonylamino-hexanoyl)-pyrrolidine-2-carbonyl]-amino}-2-phenoxymethyl-benzoylamino)-acetylamino]-acetic acid ethyl ester

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