(8S,11R,14R)-11-(4-Fluoro-3-nitro-benzyl)-5,18-dimethoxy-10,13-dioxo-14-(2,2,2-trifluoro-acetylamino)-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid

Base Information

• Chemical Name: (8S,11R,14R)-11-(4-Fluoro-3-nitro-benzyl)-5,18-dimethoxy-10,13-dioxo-14-(2,2,2-trifluoro-acetylamino)-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid
• CAS No.: 391213-84-6
• Molecular Formula: C₂₉H₂₄F₄N₄O₁₀
• Molecular Weight: 664.524
• Mol file: 391213-84-6.mol

Synonyms:(8S,11R,14R)-11-(4-Fluoro-3-nitro-benzyl)-5,18-dimethoxy-10,13-dioxo-14-(2,2,2-trifluoro-acetylamino)-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid

Chemical Property of (8S,11R,14R)-11-(4-Fluoro-3-nitro-benzyl)-5,18-dimethoxy-10,13-dioxo-14-(2,2,2-trifluoro-acetylamino)-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (8S,11R,14R)-11-(4-Fluoro-3-nitro-benzyl)-5,18-dimethoxy-10,13-dioxo-14-(2,2,2-trifluoro-acetylamino)-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaene-8-carboxylic acid

There total 24 articles about (8S,11R,14R)-11-(4-Fluoro-3-nitro-benzyl)-5,18-dimethoxy-10,13-dioxo-14-(2,2,2-trifluoro-acetylamino)-2-oxa-9,12-diaza-tricyclo[13.3.1.1^3,7]icosa-1⁽¹⁸⁾,3⁽²⁰⁾,4,6,15⁽¹⁹⁾,16-hexaene-8-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:

4-fluoro-3-nitrobenzaldehyde (42564-51-2) → (8S,11R,14R)-11-(4-Fluoro-3-nitro-benzyl)-5,18-dimethoxy-10,13-dioxo-14-(2,2,2-trifluoro-acetylamino)-2-oxa-9,12-diaza-tricyclo[13.3.1.13,7]icosa-1(18),3(20),4,6,15(19),16-hexaene-8-carboxylic acid (391213-84-6)

Guidance literature:

Multi-step reaction with 13 steps

1.1: 99 percent / TMG / tetrahydrofuran

2.1: H₂; chiral Rh(I) complex / tetrahydrofuran / 20 °C / 760.05 Torr

3.1: DMAP / tetrahydrofuran / 20 °C

3.2: 88 percent / N₂H₄ / methanol / 20 °C

4.1: TFA; DMS / CH₂Cl₂ / 0 °C

5.1: 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide; 1-hydroxy-7-azabenzotriazole / tetrahydrofuran / 0 - 20 °C

6.1: TFA; DMS / CH₂Cl₂ / 0 °C

7.1: 2,6-lutidine / CH₂Cl₂ / 0 °C

8.1: 80 percent / Cu(OAc)2; pyridine; O₂ / CH₂Cl₂ / 20 °C

9.1: 99 percent / LiOH / methanol; H₂O / 0 °C

10.1: TFA; DMS / CH₂Cl₂ / 0 °C

11.1: HATU; HOAt / CH₂Cl₂; dimethylformamide / 0 - 20 °C

12.1: N₂O₄ / dimethylformamide / 0 °C

13.1: H₂O / dimethylformamide / 6 h / 60 °C

With pyridine; 2,6-dimethylpyridine; dmap; lithium hydroxide; 1-hydroxy-7-aza-benzotriazole; copper diacetate; 2,3-dimercapto-succinic acid; water; hydrogen; oxygen; dinitrogen tetraoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; N,N,N',N'-tetramethylguanidine; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

DOI:10.1021/ja011943e

Reference yield:

C30H26F4N6O10 → (8S,11R,14R)-11-(4-Fluoro-3-nitro-benzyl)-5,18-dimethoxy-10,13-dioxo-14-(2,2,2-trifluoro-acetylamino)-2-oxa-9,12-diaza-tricyclo[13.3.1.13,7]icosa-1(18),3(20),4,6,15(19),16-hexaene-8-carboxylic acid (391213-84-6)

Guidance literature:

With water; In N,N-dimethyl-formamide; at 60 ℃; for 6h;

DOI:10.1021/ja011943e

Reference yield:

2-(3-benzyloxy-4-methoxyphenyl)ethylene (68360-39-4) → (8S,11R,14R)-11-(4-Fluoro-3-nitro-benzyl)-5,18-dimethoxy-10,13-dioxo-14-(2,2,2-trifluoro-acetylamino)-2-oxa-9,12-diaza-tricyclo[13.3.1.13,7]icosa-1(18),3(20),4,6,15(19),16-hexaene-8-carboxylic acid (391213-84-6)

Guidance literature:

Multi-step reaction with 12 steps

1: K₂OsO₂(OH)4; (DHQD)2PHAL / propan-1-ol; H₂O

2: TEMPO; NaOCl; KBr / acetone; H₂O

3: 100 percent / H₂ / Pd/C / ethanol / 760.05 Torr

4: 1-[3-(dimethylamino)propyl]-3-ethylcarbodiimide; 1-hydroxy-7-azabenzotriazole / tetrahydrofuran / 0 - 20 °C

5: TFA; DMS / CH₂Cl₂ / 0 °C

6: 2,6-lutidine / CH₂Cl₂ / 0 °C

7: 80 percent / Cu(OAc)2; pyridine; O₂ / CH₂Cl₂ / 20 °C

8: 99 percent / LiOH / methanol; H₂O / 0 °C

9: TFA; DMS / CH₂Cl₂ / 0 °C

10: HATU; HOAt / CH₂Cl₂; dimethylformamide / 0 - 20 °C

11: N₂O₄ / dimethylformamide / 0 °C

12: H₂O / dimethylformamide / 6 h / 60 °C

With pyridine; 2,6-dimethylpyridine; 2,2,6,6-tetramethyl-piperidine-N-oxyl; lithium hydroxide; sodium hypochlorite; 1-hydroxy-7-aza-benzotriazole; copper diacetate; potassium dioxotetrahydroxoosmate(VI); 2,3-dimercapto-succinic acid; water; hydrogen; oxygen; dinitrogen tetraoxide; N-(3-dimethylaminopropyl)-N-ethylcarbodiimide; 1,4-bis(9-O-dihydroquinidine)phthalazine; trifluoroacetic acid; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; potassium bromide; palladium on activated charcoal; In tetrahydrofuran; methanol; propan-1-ol; ethanol; dichloromethane; water; N,N-dimethyl-formamide; acetone; 1: Sharpless asymmetric amino-hydroxylation;

DOI:10.1021/ja011943e

upstream raw materials:

2-(3-benzyloxy-4-methoxyphenyl)ethylene

4-fluoro-3-nitrobenzaldehyde

D-(4-fluoro-3-nitrophenyl)glycine methyl ester

(R)-N-(tert-butoxycarbonyl)-4-fluoro-3-nitrophenylalanine methyl ester