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

Base Information

• Chemical Name: 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
• CAS No.: 199486-39-0
• Molecular Formula: C₂₆H₂₄N₂O₆
• Molecular Weight: 460.486

Synonyms: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

Chemical Property of 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

Chemical Property:

Purity/Quality:

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Technology Process of 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

There total 12 articles about 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 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: 40.0%

(11R,14S)-18-Amino-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 methyl ester → 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)

Guidance literature:

With tert.-butylnitrite; In N,N-dimethyl-formamide;

DOI:10.1016/S0040-4039(97)10217-9

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) → 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)

Guidance literature:

Multi-step reaction with 4 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

With 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 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) → 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)

Guidance literature:

Multi-step reaction with 3 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

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

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

upstream raw materials:

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

N-(tert-butoxycarbonyl)-D-(4-hydroxyphenyl)glycine

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

(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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