(2'S,3aS,5'R,6aS)-tert-butyl 5'-((S)-2-(4-acetoxy-3,5-dichlorobenzamido)-2-phenylethyl)-2-oxo-1'-(2,2,2-trichloroacetyl)-3a,6a-dihydrospiro[cyclopenta[d]oxazole-6,2'-pyrrolidine]-3(2H)-carboxylate

Base Information

• Chemical Name: (2'S,3aS,5'R,6aS)-tert-butyl 5'-((S)-2-(4-acetoxy-3,5-dichlorobenzamido)-2-phenylethyl)-2-oxo-1'-(2,2,2-trichloroacetyl)-3a,6a-dihydrospiro[cyclopenta[d]oxazole-6,2'-pyrrolidine]-3(2H)-carboxylate
• CAS No.: 1362209-81-1
• Molecular Formula: C₃₃H₃₂Cl₅N₃O₈
• Molecular Weight: 775.897
• Mol file: 1362209-81-1.mol

Synonyms:(2'S,3aS,5'R,6aS)-tert-butyl 5'-((S)-2-(4-acetoxy-3,5-dichlorobenzamido)-2-phenylethyl)-2-oxo-1'-(2,2,2-trichloroacetyl)-3a,6a-dihydrospiro[cyclopenta[d]oxazole-6,2'-pyrrolidine]-3(2H)-carboxylate

Chemical Property of (2'S,3aS,5'R,6aS)-tert-butyl 5'-((S)-2-(4-acetoxy-3,5-dichlorobenzamido)-2-phenylethyl)-2-oxo-1'-(2,2,2-trichloroacetyl)-3a,6a-dihydrospiro[cyclopenta[d]oxazole-6,2'-pyrrolidine]-3(2H)-carboxylate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2'S,3aS,5'R,6aS)-tert-butyl 5'-((S)-2-(4-acetoxy-3,5-dichlorobenzamido)-2-phenylethyl)-2-oxo-1'-(2,2,2-trichloroacetyl)-3a,6a-dihydrospiro[cyclopenta[d]oxazole-6,2'-pyrrolidine]-3(2H)-carboxylate

There total 24 articles about (2'S,3aS,5'R,6aS)-tert-butyl 5'-((S)-2-(4-acetoxy-3,5-dichlorobenzamido)-2-phenylethyl)-2-oxo-1'-(2,2,2-trichloroacetyl)-3a,6a-dihydrospiro[cyclopenta[d]oxazole-6,2'-pyrrolidine]-3(2H)-carboxylate 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%

di-tert-butyl dicarbonate (24424-99-5) + 2,6-dichloro-4-(((S)-2-((2'S,3aS,5'R,6aS)-2-oxo-1'-(2,2,2-trichloroacetyl)-2,3,3a,6a-tetrahydrospiro[cyclopenta[d]oxazole-6,2'-pyrrolidin]-5'-yl)-1-phenylethyl)carbamoyl)phenyl acetate (1362209-79-7) → (2'S,3aS,5'R,6aS)-tert-butyl 5'-((S)-2-(4-acetoxy-3,5-dichlorobenzamido)-2-phenylethyl)-2-oxo-1'-(2,2,2-trichloroacetyl)-3a,6a-dihydrospiro[cyclopenta[d]oxazole-6,2'-pyrrolidine]-3(2H)-carboxylate (1362209-81-1)

Guidance literature:

With dmap; triethylamine; In dichloromethane; at 20 ℃; for 1h;

DOI:10.1021/ol300431n

Reference yield:

(R)-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-ene (1287305-45-6) → (2'S,3aS,5'R,6aS)-tert-butyl 5'-((S)-2-(4-acetoxy-3,5-dichlorobenzamido)-2-phenylethyl)-2-oxo-1'-(2,2,2-trichloroacetyl)-3a,6a-dihydrospiro[cyclopenta[d]oxazole-6,2'-pyrrolidine]-3(2H)-carboxylate (1362209-81-1)

Guidance literature:

Multi-step reaction with 16 steps

1.1: tetrahydrofuran / 4 h / 20 °C

2.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium hydroxide / tetrahydrofuran / 2 h / 20 °C

3.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / -30 - -10 °C

4.1: potassium carbonate / 5,5-dimethyl-1,3-cyclohexadiene / 0.33 h / 170 °C

5.1: pyridine hydrogenfluoride / acetonitrile / 1 h / 20 °C

6.1: sulphamoyl chloride / N,N-dimethyl acetamide; acetonitrile / 0.25 h / 20 °C

7.1: dirhodium tetraacetate; [bis(acetoxy)iodo]benzene; magnesium oxide / dichloromethane / 1 h / 40 °C

8.1: dmap; triethylamine / tetrahydrofuran / 1.5 h / 20 °C

9.1: water; sodium hydride / tetrahydrofuran; mineral oil / 0 °C

10.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / 20 °C / pH 7 / aq. phosphate buffer

11.1: dichloromethane / 0.25 h / 20 °C / Cooling with ice

12.1: methanol; potassium carbonate / dichloromethane / 2 h / 20 °C

13.1: bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; [bis(acetoxy)iodo]benzene; magnesium oxide / benzene / 12 h / 20 °C

14.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C

14.2: 20 °C

15.1: sodium hydrogencarbonate / dichloromethane / 0.67 h / 20 °C

16.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C

With methanol; dmap; dirhodium tetraacetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; [bis(acetoxy)iodo]benzene; sulphamoyl chloride; water; magnesium oxide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; In tetrahydrofuran; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; N,N-dimethyl acetamide; acetonitrile; mineral oil; benzene; 2.1: Suzuki-Miyaura coupling / 4.1: Overman rearrangement / 15.1: Schotten-Baumann reaction;

DOI:10.1021/ol300431n

Reference yield:

(1R,4S)-4-(tert-butyldimethylsilyloxy)-2-iodocyclopent-2-enol (189104-95-8) → (2'S,3aS,5'R,6aS)-tert-butyl 5'-((S)-2-(4-acetoxy-3,5-dichlorobenzamido)-2-phenylethyl)-2-oxo-1'-(2,2,2-trichloroacetyl)-3a,6a-dihydrospiro[cyclopenta[d]oxazole-6,2'-pyrrolidine]-3(2H)-carboxylate (1362209-81-1)

Guidance literature:

Multi-step reaction with 19 steps

1.1: triphenylphosphine; diethylazodicarboxylate / toluene / 18 h / -30 °C

2.1: sodium hydroxide / tetrahydrofuran; methanol; water / 0.5 h / 20 °C

3.1: N-ethyl-N,N-diisopropylamine / dichloromethane; toluene / 3.5 h / 90 °C

4.1: tetrabutyl ammonium fluoride / tetrahydrofuran / 0.33 h / 20 °C

5.1: dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; sodium hydroxide / tetrahydrofuran / 2 h / 20 °C

6.1: 1,8-diazabicyclo[5.4.0]undec-7-ene / dichloromethane / 1 h / -30 - -10 °C

7.1: potassium carbonate / 5,5-dimethyl-1,3-cyclohexadiene / 0.33 h / 170 °C

8.1: pyridine hydrogenfluoride / acetonitrile / 1 h / 20 °C

9.1: sulphamoyl chloride / N,N-dimethyl acetamide; acetonitrile / 0.25 h / 20 °C

10.1: dirhodium tetraacetate; [bis(acetoxy)iodo]benzene; magnesium oxide / dichloromethane / 1 h / 40 °C

11.1: dmap; triethylamine / tetrahydrofuran / 1.5 h / 20 °C

12.1: water; sodium hydride / tetrahydrofuran; mineral oil / 0 °C

13.1: water; 2,3-dicyano-5,6-dichloro-p-benzoquinone / dichloromethane / 2 h / 20 °C / pH 7 / aq. phosphate buffer

14.1: dichloromethane / 0.25 h / 20 °C / Cooling with ice

15.1: methanol; potassium carbonate / dichloromethane / 2 h / 20 °C

16.1: bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; [bis(acetoxy)iodo]benzene; magnesium oxide / benzene / 12 h / 20 °C

17.1: trifluoroacetic acid / dichloromethane / 3 h / 20 °C

17.2: 20 °C

18.1: sodium hydrogencarbonate / dichloromethane / 0.67 h / 20 °C

19.1: dmap; triethylamine / dichloromethane / 1 h / 20 °C

With methanol; dmap; dirhodium tetraacetate; dichloro(1,1'-bis(diphenylphosphanyl)ferrocene)palladium(II)*CH₂Cl₂; bis{rhodium[3,3'-(1,3-phenylene)bis(2,2-dimethylpropanoic acid)]}; [bis(acetoxy)iodo]benzene; sulphamoyl chloride; tetrabutyl ammonium fluoride; water; magnesium oxide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; pyridine hydrogenfluoride; 1,8-diazabicyclo[5.4.0]undec-7-ene; triethylamine; N-ethyl-N,N-diisopropylamine; triphenylphosphine; trifluoroacetic acid; 2,3-dicyano-5,6-dichloro-p-benzoquinone; sodium hydroxide; diethylazodicarboxylate; In tetrahydrofuran; methanol; 5,5-dimethyl-1,3-cyclohexadiene; dichloromethane; N,N-dimethyl acetamide; water; toluene; acetonitrile; mineral oil; benzene; 1.1: Mitsunobu reaction / 5.1: Suzuki-Miyaura coupling / 7.1: Overman rearrangement / 18.1: Schotten-Baumann reaction;

DOI:10.1021/ol300431n

upstream raw materials:

(1R,4S)-4-(tert-butyldimethylsilyloxy)-2-iodocyclopent-2-enol

(R)-3-(tert-butyldimethylsilyloxy)-5-phenylpent-1-ene

tert-butyl ((S)-2-((2R,5S,9S)-9-hydroxy-1-(2,2,2-trichloroacetyl)-1-azaspiro[4.4]non-6-en-2-yl)-1-phenylethyl)carbamate

tert-butyl ((S)-2-((2R,5S,9S)-9-(carbamoyloxy)-1-(2,2,2-trichloroacetyl)-1-azaspiro[4.4]non-6-en-2-yl)-1-phenylethyl)carbamate

Downstream raw materials:

C₂₈H₂₈Cl₅N₃O₁₄