(11R,14S)-11-(3-Iodo-4-methoxy-phenyl)-9,12-dioxo-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)-11-(3-Iodo-4-methoxy-phenyl)-9,12-dioxo-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.: 197723-40-3
• Molecular Formula: C₂₇H₂₅IN₂O₆
• Molecular Weight: 600.41

Synonyms:(11R,14S)-11-(3-Iodo-4-methoxy-phenyl)-9,12-dioxo-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)-11-(3-Iodo-4-methoxy-phenyl)-9,12-dioxo-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

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Technology Process of (11R,14S)-11-(3-Iodo-4-methoxy-phenyl)-9,12-dioxo-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 12 articles about (11R,14S)-11-(3-Iodo-4-methoxy-phenyl)-9,12-dioxo-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: 90.0%

(11R,14S)-11-(3-Iodo-4-methoxy-phenyl)-9,12-dioxo-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 (197723-38-9) → (11R,14S)-11-(3-Iodo-4-methoxy-phenyl)-9,12-dioxo-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 (197723-40-3)

Guidance literature:

With copper(I) oxide; trifluoroacetic acid; In tetrahydrofuran; acetonitrile; for 1h; Heating;

Reference yield:

(S)-2-[(R)-2-Amino-2-(3-iodo-4-methoxy-phenyl)-acetylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester (197723-32-3) → (11R,14S)-11-(3-Iodo-4-methoxy-phenyl)-9,12-dioxo-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 (197723-40-3)

Guidance literature:

Multi-step reaction with 3 steps

1: 90 percent / Et₃N; HBTU / dimethylformamide / 3 h / 0 - 25 °C

2: 67 percent / CuBr*Me₂S; K₂CO₃; pyridine / acetonitrile / 36 h / Heating

3: 90 percent / TFA; Cu₂O / tetrahydrofuran / 1 h / Heating

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

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

Reference yield:

(S)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3-iodo-4-methoxy-phenyl)-acetylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester (197723-30-1) → (11R,14S)-11-(3-Iodo-4-methoxy-phenyl)-9,12-dioxo-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 (197723-40-3)

Guidance literature:

Multi-step reaction with 4 steps

1: TFA / CH₂Cl₂ / 1 h / 0 °C

2: 90 percent / Et₃N; HBTU / dimethylformamide / 3 h / 0 - 25 °C

3: 67 percent / CuBr*Me₂S; K₂CO₃; pyridine / acetonitrile / 36 h / Heating

4: 90 percent / TFA; Cu₂O / tetrahydrofuran / 1 h / Heating

With pyridine; copper(I) oxide; copper(I) bromide dimethylsulfide complex; potassium carbonate; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; triethylamine; trifluoroacetic acid; In tetrahydrofuran; dichloromethane; N,N-dimethyl-formamide; acetonitrile; 1: Substitution / 2: Acylation / 3: Cyclization / 4: Hydrogenolysis;

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

upstream raw materials:

(11R,14S)-11-(3-Iodo-4-methoxy-phenyl)-9,12-dioxo-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

(R)-tert-Butoxycarbonylamino-(3-iodo-4-methoxy-phenyl)-acetic acid

(S)-2-[(R)-2-Amino-2-(3-iodo-4-methoxy-phenyl)-acetylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester

(S)-2-[(R)-2-tert-Butoxycarbonylamino-2-(3-iodo-4-methoxy-phenyl)-acetylamino]-3-(4-hydroxy-phenyl)-propionic acid methyl ester

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