(11R,14S)-11-(4-Hydroxy-phenyl)-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,4,6,16⁽²⁰⁾,17-hexaene-14-carboxylic acid

Base Information

• Chemical Name: (11R,14S)-11-(4-Hydroxy-phenyl)-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,4,6,16⁽²⁰⁾,17-hexaene-14-carboxylic acid
• CAS No.: 199486-36-7
• Molecular Formula: C₂₅H₂₂N₂O₆
• Molecular Weight: 446.459

Synonyms:(11R,14S)-11-(4-Hydroxy-phenyl)-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,4,6,16⁽²⁰⁾,17-hexaene-14-carboxylic acid

Chemical Property of (11R,14S)-11-(4-Hydroxy-phenyl)-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,4,6,16⁽²⁰⁾,17-hexaene-14-carboxylic acid

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Technology Process of (11R,14S)-11-(4-Hydroxy-phenyl)-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,4,6,16⁽²⁰⁾,17-hexaene-14-carboxylic acid

There total 13 articles about (11R,14S)-11-(4-Hydroxy-phenyl)-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.1^3,7]henicosa-1⁽¹⁹⁾,3⁽²¹⁾,4,6,16⁽²⁰⁾,17-hexaene-14-carboxylic acid 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: 98.0%

11(R)-11-(4-hydroxyphenyl)-9,12-dioxo-2-oxa-10,13-diaza-tricyclo-<14.2.2.13,7>heneicosa-1(19),3(21),4,6(20),17-hexaene-(14S)-14-carboxxylic acid methyl ester (199486-39-0) → (11R,14S)-11-(4-Hydroxy-phenyl)-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.13,7]henicosa-1(19),3(21),4,6,16(20),17-hexaene-14-carboxylic acid (199486-36-7)

Guidance literature:

With lithium hydroxide; In tetrahydrofuran; methanol; for 8h;

DOI:10.1016/S0040-4020(99)00171-4

Reference yield:

(S)-2-[(R)-2-tert-Butoxycarbonylamino-2-(4-hydroxy-phenyl)-acetylamino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester (178744-40-6) → (11R,14S)-11-(4-Hydroxy-phenyl)-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.13,7]henicosa-1(19),3(21),4,6,16(20),17-hexaene-14-carboxylic acid (199486-36-7)

Guidance literature:

Multi-step reaction with 5 steps

1: 1.) TFA, 2.) Et₃N, 3.) HOBT, EDC / 1) CH₂Cl₂, 0 deg C, 30 min; 2) CH₂Cl₂, 0 deg C, 10 min; 3) CH₂Cl₂, rt, 5 h

2: KHCO₃, 18-crown-6 ether / dimethylformamide / 10 h / Ambient temperature; further conditions

3: H₂ / Pd/C / methanol

4: t-BuONO / dimethylformamide / 0.25 h / 65 °C

5: 98 percent / aq. LiOH / tetrahydrofuran; methanol / 8 h

With lithium hydroxide; tert.-butylnitrite; 18-crown-6 ether; hydrogen; benzotriazol-1-ol; potassium hydrogencarbonate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; trifluoroacetic acid; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(99)00171-4

Reference yield:

(3S)-3-(4-fluoro-3-nitrophenyl)-2-<(2R)-2-(4-hydroxy-phenyl)-2-<2-(3-hydroxyphenyl)-acetylamino>acetylamino>-propionic acid methyl ester (199486-35-6) → (11R,14S)-11-(4-Hydroxy-phenyl)-9,12-dioxo-2-oxa-10,13-diaza-tricyclo[14.2.2.13,7]henicosa-1(19),3(21),4,6,16(20),17-hexaene-14-carboxylic acid (199486-36-7)

Guidance literature:

Multi-step reaction with 4 steps

1: KHCO₃, 18-crown-6 ether / dimethylformamide / 10 h / Ambient temperature; further conditions

2: H₂ / Pd/C / methanol

3: t-BuONO / dimethylformamide / 0.25 h / 65 °C

4: 98 percent / aq. LiOH / tetrahydrofuran; methanol / 8 h

With lithium hydroxide; tert.-butylnitrite; 18-crown-6 ether; hydrogen; potassium hydrogencarbonate; palladium on activated charcoal; In tetrahydrofuran; methanol; N,N-dimethyl-formamide;

DOI:10.1016/S0040-4020(99)00171-4

upstream raw materials:

11(R)-11-(4-hydroxyphenyl)-9,12-dioxo-2-oxa-10,13-diaza-tricyclo-<14.2.2.1^3,7>heneicosa-1(19),3(21),4,6(20),17-hexaene-(14S)-14-carboxxylic acid methyl ester

m-hydroxyphenylacetic acid

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

(3S)-3-(4-fluoro-3-nitrophenyl)-2-<(2R)-2-(4-hydroxy-phenyl)-2-<2-(3-hydroxyphenyl)-acetylamino>acetylamino>-propionic acid methyl ester

Downstream raw materials:

11(R)-11-(4-hydroxyphenyl)-9,12-dioxo-2-oxa-10,13-diaza-tricyclo-<14.2.2.1^3,7>heneicosa-1(19),3(21),4,6(20),17-hexaene-(14S)-14-carboxylic-3-fluoro-4-nitrobenzylamine

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