tert-butyl (1S)-1-(1H-benzimidazol-2-yl)-2-{4-[(5S)-1,1-dioxido-3-oxoisothiazolidin-5-yl]-3-fluorophenyl}ethylcarbamate

Base Information

• Chemical Name: tert-butyl (1S)-1-(1H-benzimidazol-2-yl)-2-{4-[(5S)-1,1-dioxido-3-oxoisothiazolidin-5-yl]-3-fluorophenyl}ethylcarbamate
• CAS No.: 905281-16-5
• Molecular Formula: C₂₃H₂₅FN₄O₅S
• Molecular Weight: 488.54
• Mol file: 905281-16-5.mol

Synonyms:tert-butyl (1S)-1-(1H-benzimidazol-2-yl)-2-{4-[(5S)-1,1-dioxido-3-oxoisothiazolidin-5-yl]-3-fluorophenyl}ethylcarbamate

Chemical Property of tert-butyl (1S)-1-(1H-benzimidazol-2-yl)-2-{4-[(5S)-1,1-dioxido-3-oxoisothiazolidin-5-yl]-3-fluorophenyl}ethylcarbamate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of tert-butyl (1S)-1-(1H-benzimidazol-2-yl)-2-{4-[(5S)-1,1-dioxido-3-oxoisothiazolidin-5-yl]-3-fluorophenyl}ethylcarbamate

There total 12 articles about tert-butyl (1S)-1-(1H-benzimidazol-2-yl)-2-{4-[(5S)-1,1-dioxido-3-oxoisothiazolidin-5-yl]-3-fluorophenyl}ethylcarbamate 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:

2-fluoro-4-methylphenylboronic acid (170981-26-7) → tert-butyl (1S)-1-(1H-benzimidazol-2-yl)-2-{4-[(5S)-1,1-dioxido-3-oxoisothiazolidin-5-yl]-3-fluorophenyl}ethylcarbamate (905281-16-5)

Guidance literature:

Multi-step reaction with 11 steps

1: 65 percent / triethylamine; [1,1'-bis(diphenylphosphino)ferrocene]PdCl₂*CH₂Cl₂ / toluene / 18 h / 90 °C

2: 79 percent / H₂ / Pd/C / ethanol / 24 h / 2585.74 Torr

3: 61 percent / N-bromosuccinimide; benzoyl peroxide / CCl₄ / 3.5 h / Heating

4: 83 percent / silver nitrate / ethanol; H₂O / 0.5 h / Heating

5: 77 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 20 °C

6: 531 mg / (R,R)-1,2-[(o-MeOPh)(Ph)P]2CH₂CH₂(1,5-cyclooctadiene)Rh*BF₄; H₂ / ethanol / 16 h / 2585.74 Torr

7: 0.03 h / 130 °C / microwave irradiation

8: triethylamine / 2 h / 20 °C

9: 507 mg / aq. lithium hydroxide / 2 h

10: benzotriazol-1-yloxytris(dimethylamino)phosphonium*PF₆; N,N-diisopropylethylamine / dimethylformamide / 2 h / 20 °C

11: acetic acid / 2 h / 40 °C

With (1,1'-bis(diphenylphosphino)ferrocene)palladium(II) dichloride; lithium hydroxide; N-Bromosuccinimide; (Z,Z)-cycloocta-1,5-diene(R,R-1,2-bis(2,5-diethylphospholanyl)benzene)rhodium(I) tetrafluoroborate; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; silver nitrate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; dibenzoyl peroxide; palladium on activated charcoal; In tetrachloromethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; toluene; 1: Suzuki coupling / 5: Horner-Wadsworth-Emmons olefination;

DOI:10.1021/jm0600904

Reference yield:

2-tert-butyl-5-(2-fluoro-4-methylphenyl)isothiazol-3(2H)-one 1,1-dioxide (850321-75-4) → tert-butyl (1S)-1-(1H-benzimidazol-2-yl)-2-{4-[(5S)-1,1-dioxido-3-oxoisothiazolidin-5-yl]-3-fluorophenyl}ethylcarbamate (905281-16-5)

Guidance literature:

Multi-step reaction with 10 steps

1: 79 percent / H₂ / Pd/C / ethanol / 24 h / 2585.74 Torr

2: 61 percent / N-bromosuccinimide; benzoyl peroxide / CCl₄ / 3.5 h / Heating

3: 83 percent / silver nitrate / ethanol; H₂O / 0.5 h / Heating

4: 77 percent / 1,8-diazabicyclo[5.4.0]undec-7-ene / CH₂Cl₂ / 1 h / 20 °C

5: 531 mg / (R,R)-1,2-[(o-MeOPh)(Ph)P]2CH₂CH₂(1,5-cyclooctadiene)Rh*BF₄; H₂ / ethanol / 16 h / 2585.74 Torr

6: 0.03 h / 130 °C / microwave irradiation

7: triethylamine / 2 h / 20 °C

8: 507 mg / aq. lithium hydroxide / 2 h

9: benzotriazol-1-yloxytris(dimethylamino)phosphonium*PF₆; N,N-diisopropylethylamine / dimethylformamide / 2 h / 20 °C

10: acetic acid / 2 h / 40 °C

With lithium hydroxide; N-Bromosuccinimide; (Z,Z)-cycloocta-1,5-diene(R,R-1,2-bis(2,5-diethylphospholanyl)benzene)rhodium(I) tetrafluoroborate; hydrogen; (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; silver nitrate; acetic acid; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; dibenzoyl peroxide; palladium on activated charcoal; In tetrachloromethane; ethanol; dichloromethane; water; N,N-dimethyl-formamide; 4: Horner-Wadsworth-Emmons olefination;

DOI:10.1021/jm0600904

Reference yield:

{(R)-1-(2-Amino-phenylcarbamoyl)-2-[3-fluoro-4-((S)-1,1,3-trioxo-1λ6-isothiazolidin-5-yl)-phenyl]-ethyl}-carbamic acid tert-butyl ester → tert-butyl (1S)-1-(1H-benzimidazol-2-yl)-2-{4-[(5S)-1,1-dioxido-3-oxoisothiazolidin-5-yl]-3-fluorophenyl}ethylcarbamate (905281-16-5)

Guidance literature:

With acetic acid; at 40 ℃; for 2h;

DOI:10.1021/jm0600904

upstream raw materials:

2-fluoro-4-methylphenylboronic acid

2-tert-butyl-5-(2-fluoro-4-methylphenyl)isothiazol-3(2H)-one 1,1-dioxide

2-tert-butyl-5-(2-fluoro-4-methylphenyl)isothiazolidin-3-one 1,1-dioxide

4-(2-tert-butyl-1,1-dioxido-3-oxoisothiazolidin-5-yl)-3-fluorobenzaldehyde