(8R,11R,14S)-11-(3,5-Dichloro-4-hydroxy-phenyl)-4-hydroxy-13-methyl-9,12-dioxo-8-(2,2,2-trifluoro-acetylamino)-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: (8R,11R,14S)-11-(3,5-Dichloro-4-hydroxy-phenyl)-4-hydroxy-13-methyl-9,12-dioxo-8-(2,2,2-trifluoro-acetylamino)-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.: 586413-70-9
• Molecular Formula: C₂₈H₂₂Cl₂F₃N₃O₈
• Molecular Weight: 656.399

Synonyms:(8R,11R,14S)-11-(3,5-Dichloro-4-hydroxy-phenyl)-4-hydroxy-13-methyl-9,12-dioxo-8-(2,2,2-trifluoro-acetylamino)-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 (8R,11R,14S)-11-(3,5-Dichloro-4-hydroxy-phenyl)-4-hydroxy-13-methyl-9,12-dioxo-8-(2,2,2-trifluoro-acetylamino)-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:

Purity/Quality:

Safty Information:

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Technology Process of (8R,11R,14S)-11-(3,5-Dichloro-4-hydroxy-phenyl)-4-hydroxy-13-methyl-9,12-dioxo-8-(2,2,2-trifluoro-acetylamino)-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 12 articles about (8R,11R,14S)-11-(3,5-Dichloro-4-hydroxy-phenyl)-4-hydroxy-13-methyl-9,12-dioxo-8-(2,2,2-trifluoro-acetylamino)-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:

(8R,11R,14S)-11-(3,5-Dichloro-4-methoxy-phenyl)-4-methoxy-13-methyl-9,12-dioxo-8-(2,2,2-trifluoro-acetylamino)-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 (586413-69-6) → (8R,11R,14S)-11-(3,5-Dichloro-4-hydroxy-phenyl)-4-hydroxy-13-methyl-9,12-dioxo-8-(2,2,2-trifluoro-acetylamino)-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 (586413-70-9)

Guidance literature:

With aluminum tri-bromide; ethanethiol; at 0 ℃; for 1.5h;

DOI:10.1021/ja030249r

Reference yield:

isovanillin (621-59-0) → (8R,11R,14S)-11-(3,5-Dichloro-4-hydroxy-phenyl)-4-hydroxy-13-methyl-9,12-dioxo-8-(2,2,2-trifluoro-acetylamino)-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 (586413-70-9)

Guidance literature:

Multi-step reaction with 10 steps

1: 98 percent / imidazole / dimethylformamide / 0.5 h

2: 98 percent / MgSO₄ / benzene / 24 h

3: Ti(O-i-Pr)4; chiral amino acid ligand; isopropanol / toluene / 4 h

4: 3.11 g / NaHCO₃; 1-hydroxy-7-azabenzotriazole; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide / tetrahydrofuran; dimethylformamide / 12 h / 22 °C

5: NH₄OAc; aq. NaIO₄ / acetone / 12 h / 22 °C

6: 650 mg / Cu(OAc)2; 4A molecular sieves; Et₃N / CH₂Cl₂; methanol / 6 h / 22 °C

7: 98 percent / HCl / methanol / 1.5 h / 22 °C

8: 860 mg / 2,6-lutidine / CH₂Cl₂ / 2 h

9: 1.0 g / AlBr₃; EtSH / 1.5 h / 0 °C

With 1H-imidazole; 2,6-dimethylpyridine; titanium(IV) isopropylate; hydrogenchloride; sodium periodate; 1-hydroxy-7-aza-benzotriazole; aluminum tri-bromide; copper diacetate; 4 A molecular sieve; chiral amino acid ligand; ammonium acetate; sodium hydrogencarbonate; magnesium sulfate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; isopropyl alcohol; ethanethiol; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1021/ja030249r

Reference yield:

p-methoxy-m-(tert-butyldimethylsilyloxy)-benzaldehyde (97315-18-9) → (8R,11R,14S)-11-(3,5-Dichloro-4-hydroxy-phenyl)-4-hydroxy-13-methyl-9,12-dioxo-8-(2,2,2-trifluoro-acetylamino)-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 (586413-70-9)

Guidance literature:

Multi-step reaction with 9 steps

1: 98 percent / MgSO₄ / benzene / 24 h

2: Ti(O-i-Pr)4; chiral amino acid ligand; isopropanol / toluene / 4 h

3: 3.11 g / NaHCO₃; 1-hydroxy-7-azabenzotriazole; 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide / tetrahydrofuran; dimethylformamide / 12 h / 22 °C

4: NH₄OAc; aq. NaIO₄ / acetone / 12 h / 22 °C

5: 650 mg / Cu(OAc)2; 4A molecular sieves; Et₃N / CH₂Cl₂; methanol / 6 h / 22 °C

6: 98 percent / HCl / methanol / 1.5 h / 22 °C

7: 860 mg / 2,6-lutidine / CH₂Cl₂ / 2 h

8: 1.0 g / AlBr₃; EtSH / 1.5 h / 0 °C

With 2,6-dimethylpyridine; titanium(IV) isopropylate; hydrogenchloride; sodium periodate; 1-hydroxy-7-aza-benzotriazole; aluminum tri-bromide; copper diacetate; 4 A molecular sieve; chiral amino acid ligand; ammonium acetate; sodium hydrogencarbonate; magnesium sulfate; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; isopropyl alcohol; ethanethiol; In tetrahydrofuran; methanol; dichloromethane; N,N-dimethyl-formamide; acetone; toluene; benzene;

DOI:10.1021/ja030249r

upstream raw materials:

(8R,11R,14S)-11-(3,5-Dichloro-4-methoxy-phenyl)-4-methoxy-13-methyl-9,12-dioxo-8-(2,2,2-trifluoro-acetylamino)-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 methyl ester

isovanillin

p-methoxy-m-(tert-butyldimethylsilyloxy)-benzaldehyde

(R)-N-Boc-m-hydroxy-p-methoxyphenyl-Gly

Downstream raw materials:

(R)-{[(8R,11R,14S)-8-Amino-11-(3,5-dichloro-4-hydroxy-phenyl)-4-hydroxy-5-iodo-13-methyl-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-carbonyl]-amino}-(4-hydroxy-phenyl)-acetic acid methyl ester

C₄₃H₄₄Cl₂F₃IN₄O₁₀Si

C₄₈H₄₄Cl₄IN₅O₁₃

C₅₉H₅₃Cl₄N₇O₁₄

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