(11R,14S)-5-Bromo-9,12-dioxo-11-phenyl-4-(pyrrolidin-1-ylazo)-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester

Base Information

• Chemical Name: (11R,14S)-5-Bromo-9,12-dioxo-11-phenyl-4-(pyrrolidin-1-ylazo)-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester
• CAS No.: 250160-50-0
• Molecular Formula: C₃₀H₃₀BrN₅O₅
• Molecular Weight: 620.503
• Mol file: 250160-50-0.mol

Synonyms:(11R,14S)-5-Bromo-9,12-dioxo-11-phenyl-4-(pyrrolidin-1-ylazo)-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester

Chemical Property of (11R,14S)-5-Bromo-9,12-dioxo-11-phenyl-4-(pyrrolidin-1-ylazo)-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (11R,14S)-5-Bromo-9,12-dioxo-11-phenyl-4-(pyrrolidin-1-ylazo)-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester

There total 11 articles about (11R,14S)-5-Bromo-9,12-dioxo-11-phenyl-4-(pyrrolidin-1-ylazo)-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl 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: 77.0%

(S)-2-((R)-2-{2-[3,5-Dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-acetylamino}-2-phenyl-acetylamino)-3-(4-hydroxy-phenyl)-propionic acid methyl ester (250160-49-7) → (11R,14S)-5-Bromo-9,12-dioxo-11-phenyl-4-(pyrrolidin-1-ylazo)-2-oxa-10,13-diaza-tricyclo[14.2.2.13,7]henicosa-1(19),3,5,7(21),16(20),17-hexaene-14-carboxylic acid methyl ester (250160-50-0)

Guidance literature:

With pyridine; copper(I) bromide dimethylsulfide complex; potassium carbonate; In acetonitrile; at 75 ℃; for 15h;

DOI:10.1021/ja9636350

Reference yield:

L-Tyr-OMe (1080-06-4) → (11R,14S)-5-Bromo-9,12-dioxo-11-phenyl-4-(pyrrolidin-1-ylazo)-2-oxa-10,13-diaza-tricyclo[14.2.2.13,7]henicosa-1(19),3,5,7(21),16(20),17-hexaene-14-carboxylic acid methyl ester (250160-50-0)

Guidance literature:

Multi-step reaction with 4 steps

1: 91 percent / EDC; HOBt / dimethylformamide / 10 h / 0 °C

2: H₂ / 10 percent Pd(OH)2/C / methanol / 1 h / 25 °C

3: HBTU; Et₃N / dimethylformamide / 18 h / 0 °C

4: 77 percent / CuBr*Me₂S; K₂CO₃; pyridine / acetonitrile / 15 h / 75 °C

With pyridine; copper(I) bromide dimethylsulfide complex; hydrogen; potassium carbonate; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; palladium dihydroxide; In methanol; N,N-dimethyl-formamide; acetonitrile; 1: Acylation / 2: Hydrogenolysis / 3: Acylation / 4: Cyclization;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2584::AID-CHEM2584>3.0.CO;2-B

Reference yield:

(S)-2-((R)-2-Benzyloxycarbonylamino-2-phenyl-acetylamino)-3-(4-hydroxy-phenyl)-propionic acid methyl ester (188966-58-7) → (11R,14S)-5-Bromo-9,12-dioxo-11-phenyl-4-(pyrrolidin-1-ylazo)-2-oxa-10,13-diaza-tricyclo[14.2.2.13,7]henicosa-1(19),3,5,7(21),16(20),17-hexaene-14-carboxylic acid methyl ester (250160-50-0)

Guidance literature:

Multi-step reaction with 3 steps

1: H₂ / 10 percent Pd(OH)2/C / methanol / 1 h / 25 °C

2: HBTU; Et₃N / dimethylformamide / 18 h / 0 °C

3: 77 percent / CuBr*Me₂S; K₂CO₃; pyridine / acetonitrile / 15 h / 75 °C

With pyridine; copper(I) bromide dimethylsulfide complex; hydrogen; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; palladium dihydroxide; In methanol; N,N-dimethyl-formamide; acetonitrile; 1: Hydrogenolysis / 2: Acylation / 3: Cyclization;

DOI:10.1002/(SICI)1521-3765(19990903)5:9<2584::AID-CHEM2584>3.0.CO;2-B

upstream raw materials:

(S)-2-((R)-2-{2-[3,5-Dibromo-4-(pyrrolidin-1-ylazo)-phenyl]-acetylamino}-2-phenyl-acetylamino)-3-(4-hydroxy-phenyl)-propionic acid methyl ester

L-Tyr-OMe

Z-D-phenylglycine

3,5-dibromo-4-aminophenethyl alcohol

Downstream raw materials:

(11R,14S)-4-Amino-9,12-dioxo-11-phenyl-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3,5,7⁽²¹⁾,16⁽²⁰⁾,17-hexaene-14-carboxylic acid methyl ester