2-[(14-tert-butoxycarbonylamino-11-sec-butyl-3,4-dihydroxy-19-methoxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]heneicosa-1⁽²⁰⁾,2,4,6⁽²¹⁾,16,18-hexaene-8-carbonyl)-amino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester

Base Information

• Chemical Name: 2-[(14-tert-butoxycarbonylamino-11-sec-butyl-3,4-dihydroxy-19-methoxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]heneicosa-1⁽²⁰⁾,2,4,6⁽²¹⁾,16,18-hexaene-8-carbonyl)-amino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester
• CAS No.: 351442-21-2
• Molecular Formula: C₄₀H₄₈FN₅O₁₂
• Molecular Weight: 809.846

Synonyms:2-[(14-tert-butoxycarbonylamino-11-sec-butyl-3,4-dihydroxy-19-methoxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]heneicosa-1⁽²⁰⁾,2,4,6⁽²¹⁾,16,18-hexaene-8-carbonyl)-amino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester

Chemical Property of 2-[(14-tert-butoxycarbonylamino-11-sec-butyl-3,4-dihydroxy-19-methoxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]heneicosa-1⁽²⁰⁾,2,4,6⁽²¹⁾,16,18-hexaene-8-carbonyl)-amino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester

Chemical Property:

Purity/Quality:

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Technology Process of 2-[(14-tert-butoxycarbonylamino-11-sec-butyl-3,4-dihydroxy-19-methoxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]heneicosa-1⁽²⁰⁾,2,4,6⁽²¹⁾,16,18-hexaene-8-carbonyl)-amino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester

There total 20 articles about 2-[(14-tert-butoxycarbonylamino-11-sec-butyl-3,4-dihydroxy-19-methoxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]heneicosa-1⁽²⁰⁾,2,4,6⁽²¹⁾,16,18-hexaene-8-carbonyl)-amino]-3-(4-fluoro-3-nitro-phenyl)-propionic 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: 82.0%

di-tert-butyl dicarbonate (24424-99-5) + 2-[(14-tert-butoxycarbonylamino-11-sec-butyl-3,4-diisopropoxy-19-methoxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.12,6]heneicosa-1(19),2,4,6(21),16(20),17-hexaene-8-carbonyl)-amino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester → 2-[(14-tert-butoxycarbonylamino-11-sec-butyl-3,4-dihydroxy-19-methoxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.12,6]heneicosa-1(20),2,4,6(21),16,18-hexaene-8-carbonyl)-amino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester (351442-21-2)

Guidance literature:

2-[(14-tert-butoxycarbonylamino-11-sec-butyl-3,4-diisopropoxy-19-methoxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.1^2,6]heneicosa-1⁽¹⁹⁾,2,4,6⁽²¹⁾,16⁽²⁰⁾,17-hexaene-8-carbonyl)-amino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester; With boron trichloride; In dichloromethane; at 20 ℃; for 4h;

di-tert-butyl dicarbonate; With sodium hydrogencarbonate; In 1,4-dioxane; water; Further stages.;

DOI:10.1021/ol016021v

Reference yield:

3-bromo-4,5-dihydroxybenzaldehyde (16414-34-9) → 2-[(14-tert-butoxycarbonylamino-11-sec-butyl-3,4-dihydroxy-19-methoxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.12,6]heneicosa-1(20),2,4,6(21),16,18-hexaene-8-carbonyl)-amino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester (351442-21-2)

Guidance literature:

Multi-step reaction with 17 steps

1.1: 83 percent / K₂CO₃ / dimethylsulfoxide / 120 h / 55 °C

2.1: 91 percent / p-TsOH / benzene / 5 h / Heating

3.1: BuLi / tetrahydrofuran; hexane / 0.67 h / -78 °C

3.2: B(OMe)3 / tetrahydrofuran; hexane / 15 h / 20 °C

3.3: 67 percent / HCl / tetrahydrofuran; hexane; H₂O / 2 h

4.1: Na₂CO₃ / Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O / 0.08 h / 20 °C

4.2: 85 percent / 1,2-dimethoxy-ethane; H₂O / 16 h / 95 °C

5.1: 80 percent / NaBH₄ / tetrahydrofuran / 1 h / -78 °C

6.1: triethylamine / CH₂Cl₂ / 2 h / 20 °C

7.1: 2.0 g / LiBr / acetone; CH₂Cl₂ / 16 h / 20 °C

8.1: CsOH*H₂O; N-methyl antracene-O-allyl cinchonidinium bromide / CH₂Cl₂ / 20 h / -50 °C

9.1: 294.0 mg / citric acid; silica gel / H₂O; tetrahydrofuran / 2 h

10.1: 90 percent / EDC; HOBt / CH₂Cl₂ / 15 h / 20 °C

11.1: 100 percent / LiOH / tetrahydrofuran; H₂O / 5 h / 20 °C / Saponification

12.1: 81 percent / EDC / CH₂Cl₂ / 4 h / 20 °C

13.1: 87 percent / diisoproylethylamine; cyclohexene / Pd/C / 2-methyl-propan-2-ol / 17 h / 85 °C

14.1: TFA / 5 h / 20 °C

15.1: 100 percent / NaHCO₃ / dioxane; H₂O

16.1: 92 percent / EDC; HOBt / CH₂Cl₂ / 15 h / 20 °C

17.1: BCl₃ / CH₂Cl₂ / 4 h / 20 °C

17.2: 82 percent / NaHCO₃ / dioxane; H₂O

With cesium hydroxide; lithium hydroxide; sodium tetrahydroborate; n-butyllithium; N-methyl antracene-O-allyl cinchonidinium bromide; silica gel; boron trichloride; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; citric acid; lithium bromide; cyclohexene; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; hexane; dichloromethane; water; dimethyl sulfoxide; acetone; tert-butyl alcohol; benzene; 4.1: Suzuki cross-coupling reaction / 7.1: Finkelstein bromination reaction;

DOI:10.1021/ol016021v

Reference yield:

5-bromo-4-hydroxy-3-methoxybenzaldehyde (2973-76-4) → 2-[(14-tert-butoxycarbonylamino-11-sec-butyl-3,4-dihydroxy-19-methoxy-10,13-dioxo-9,12-diaza-tricyclo[14.3.1.12,6]heneicosa-1(20),2,4,6(21),16,18-hexaene-8-carbonyl)-amino]-3-(4-fluoro-3-nitro-phenyl)-propionic acid methyl ester (351442-21-2)

Guidance literature:

Multi-step reaction with 18 steps

1.1: 98 percent / AlCl₃; pyridine / CH₂Cl₂ / 24 h / 40 °C

2.1: 83 percent / K₂CO₃ / dimethylsulfoxide / 120 h / 55 °C

3.1: 91 percent / p-TsOH / benzene / 5 h / Heating

4.1: BuLi / tetrahydrofuran; hexane / 0.67 h / -78 °C

4.2: B(OMe)3 / tetrahydrofuran; hexane / 15 h / 20 °C

4.3: 67 percent / HCl / tetrahydrofuran; hexane; H₂O / 2 h

5.1: Na₂CO₃ / Pd(PPh₃)4 / 1,2-dimethoxy-ethane; H₂O / 0.08 h / 20 °C

5.2: 85 percent / 1,2-dimethoxy-ethane; H₂O / 16 h / 95 °C

6.1: 80 percent / NaBH₄ / tetrahydrofuran / 1 h / -78 °C

7.1: triethylamine / CH₂Cl₂ / 2 h / 20 °C

8.1: 2.0 g / LiBr / acetone; CH₂Cl₂ / 16 h / 20 °C

9.1: CsOH*H₂O; N-methyl antracene-O-allyl cinchonidinium bromide / CH₂Cl₂ / 20 h / -50 °C

10.1: 294.0 mg / citric acid; silica gel / H₂O; tetrahydrofuran / 2 h

11.1: 90 percent / EDC; HOBt / CH₂Cl₂ / 15 h / 20 °C

12.1: 100 percent / LiOH / tetrahydrofuran; H₂O / 5 h / 20 °C / Saponification

13.1: 81 percent / EDC / CH₂Cl₂ / 4 h / 20 °C

14.1: 87 percent / diisoproylethylamine; cyclohexene / Pd/C / 2-methyl-propan-2-ol / 17 h / 85 °C

15.1: TFA / 5 h / 20 °C

16.1: 100 percent / NaHCO₃ / dioxane; H₂O

17.1: 92 percent / EDC; HOBt / CH₂Cl₂ / 15 h / 20 °C

18.1: BCl₃ / CH₂Cl₂ / 4 h / 20 °C

18.2: 82 percent / NaHCO₃ / dioxane; H₂O

With pyridine; cesium hydroxide; lithium hydroxide; sodium tetrahydroborate; n-butyllithium; aluminium trichloride; N-methyl antracene-O-allyl cinchonidinium bromide; silica gel; boron trichloride; sodium hydrogencarbonate; sodium carbonate; potassium carbonate; benzotriazol-1-ol; toluene-4-sulfonic acid; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic acid; citric acid; lithium bromide; cyclohexene; palladium on activated charcoal; tetrakis(triphenylphosphine) palladium⁽⁰⁾; In tetrahydrofuran; 1,4-dioxane; 1,2-dimethoxyethane; hexane; dichloromethane; water; dimethyl sulfoxide; acetone; tert-butyl alcohol; benzene; 5.1: Suzuki cross-coupling reaction / 8.1: Finkelstein bromination reaction;

DOI:10.1021/ol016021v

upstream raw materials:

di-tert-butyl dicarbonate

3-bromo-4,5-dihydroxybenzaldehyde

5-bromo-4-hydroxy-3-methoxybenzaldehyde

vanillin

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