(2S)-N-((3S,6S)-3-(tert-butyl)-1⁹-fluoro-2⁴-(4-(hydroxymethyl)oxazol-2-yl)-5-oxo-1^5a,1^10bdihydro-1⁶H-4-aza-1(10b,2)-benzofuro[2,3-b]indola-2(5,2)-oxazolacycloheptaphane-6-yl)-2-hydroxy-3-methylbutanamide

Base Information

• Chemical Name: (2S)-N-((3S,6S)-3-(tert-butyl)-1⁹-fluoro-2⁴-(4-(hydroxymethyl)oxazol-2-yl)-5-oxo-1^5a,1^10bdihydro-1⁶H-4-aza-1(10b,2)-benzofuro[2,3-b]indola-2(5,2)-oxazolacycloheptaphane-6-yl)-2-hydroxy-3-methylbutanamide
• CAS No.: 1403850-91-8
• Molecular Formula: C₃₄H₃₆FN₅O₇
• Molecular Weight: 645.688

Synonyms:

Chemical Property of (2S)-N-((3S,6S)-3-(tert-butyl)-1⁹-fluoro-2⁴-(4-(hydroxymethyl)oxazol-2-yl)-5-oxo-1^5a,1^10bdihydro-1⁶H-4-aza-1(10b,2)-benzofuro[2,3-b]indola-2(5,2)-oxazolacycloheptaphane-6-yl)-2-hydroxy-3-methylbutanamide

Chemical Property:

Purity/Quality:

PPI-2206 ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

• Uses: A diazonamide analog for treatment of cancer and other proliferative disorders.

Technology Process of (2S)-N-((3S,6S)-3-(tert-butyl)-1⁹-fluoro-2⁴-(4-(hydroxymethyl)oxazol-2-yl)-5-oxo-1^5a,1^10bdihydro-1⁶H-4-aza-1(10b,2)-benzofuro[2,3-b]indola-2(5,2)-oxazolacycloheptaphane-6-yl)-2-hydroxy-3-methylbutanamide

There total 16 articles about (2S)-N-((3S,6S)-3-(tert-butyl)-1⁹-fluoro-2⁴-(4-(hydroxymethyl)oxazol-2-yl)-5-oxo-1^5a,1^10bdihydro-1⁶H-4-aza-1(10b,2)-benzofuro[2,3-b]indola-2(5,2)-oxazolacycloheptaphane-6-yl)-2-hydroxy-3-methylbutanamide 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: 91.0%

(S)-2-Hydroxy-3-methylbutanoic acid (17407-55-5) + (3S,6S)-6-amino-3-(tert-butyl)-19-fluoro-24-(4-(hydroxymethyl)oxazol-2-yl)-15a,110b-dihydro-16H-4-aza-1(10b,2)-benzofuro[2,3-b]indola-2(5,2)-oxazolacycloheptaphan-5-one → (2S)-N-((3S,6S)-3-(tert-butyl)-19-fluoro-24-(4-(hydroxymethyl)oxazol-2-yl)-5-oxo-15a,110bdihydro-16H-4-aza-1(10b,2)-benzofuro[2,3-b]indola-2(5,2)-oxazolacycloheptaphane-6-yl)-2-hydroxy-3-methylbutanamide (1403850-91-8)

Guidance literature:

With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 20 ℃; for 4.5h; Inert atmosphere;

DOI:10.1002/anie.201411663

Reference yield:

C35H36FN5O8 (1403851-26-2) → (2S)-N-((3S,6S)-3-(tert-butyl)-19-fluoro-24-(4-(hydroxymethyl)oxazol-2-yl)-5-oxo-15a,110bdihydro-16H-4-aza-1(10b,2)-benzofuro[2,3-b]indola-2(5,2)-oxazolacycloheptaphane-6-yl)-2-hydroxy-3-methylbutanamide (1403850-91-8)

Guidance literature:

C₃₅H₃₆FN₅O₈; With lithium borohydride; isopropyl alcohol; In tetrahydrofuran; at 0 - 20 ℃; for 22h;

With water; ammonium chloride; In tetrahydrofuran; isopropyl alcohol; for 1h;

Reference yield:

DL-5-fluorotryptophan (154-08-5,343-91-9,97749-24-1) → (2S)-N-((3S,6S)-3-(tert-butyl)-19-fluoro-24-(4-(hydroxymethyl)oxazol-2-yl)-5-oxo-15a,110bdihydro-16H-4-aza-1(10b,2)-benzofuro[2,3-b]indola-2(5,2)-oxazolacycloheptaphane-6-yl)-2-hydroxy-3-methylbutanamide (1403850-91-8)

Guidance literature:

Multi-step reaction with 13 steps

1.1: chloro-trimethyl-silane / 20 h / 0 - 20 °C

2.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 0 - 20 °C

3.1: 2,3-dicyano-5,6-dichloro-p-benzoquinone / tetrahydrofuran / 1 h / 85 °C

4.1: hydrogen / palladium 10% on activated carbon / methanol / 1 h

5.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 0 - 20 °C

6.1: potassium carbonate; N,N,N,N-tetraethylammonium tetrafluoroborate / N,N-dimethyl-formamide; water / 72 h / Electrochemical reaction

7.1: water; lithium hydroxide / methanol / 18 h / 20 °C / Cooling with ice

7.2: 10 °C

8.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 0 - 20 °C

9.1: (bis-(2-methoxyethyl)amino)sulfur trufluoride / dichloromethane / -20 - 20 °C

10.1: Bromotrichloromethane; 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 0 - 20 °C

11.1: hydrogen; tert-butylamine / palladium 10% on activated carbon / methanol / 4 h

12.1: N-ethyl-N,N-diisopropylamine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; benzotriazol-1-ol / N,N-dimethyl-formamide / 16 h / 0 - 20 °C

13.1: isopropyl alcohol; lithium borohydride / tetrahydrofuran / 22 h / 0 - 20 °C

13.2: 1 h

With lithium borohydride; chloro-trimethyl-silane; Bromotrichloromethane; water; hydrogen; N,N,N,N-tetraethylammonium tetrafluoroborate; potassium carbonate; benzotriazol-1-ol; 1,8-diazabicyclo[5.4.0]undec-7-ene; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; tert-butylamine; N-ethyl-N,N-diisopropylamine; isopropyl alcohol; 2,3-dicyano-5,6-dichloro-p-benzoquinone; lithium hydroxide; (bis-(2-methoxyethyl)amino)sulfur trufluoride; palladium 10% on activated carbon; In tetrahydrofuran; methanol; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

DL-5-fluorotryptophan

C₂₆H₃₀FN₃O₅

C₂₆H₂₆FN₃O₅

C₁₈H₂₀FN₃O₃

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