[(3R,5R)-3-[(3-Chloro-benzylcarbamoyl)-methyl]-5-(2,4-dichloro-phenyl)-2-oxo-pyrrolidin-1-yl]-acetic acid

Base Information

• Chemical Name: [(3R,5R)-3-[(3-Chloro-benzylcarbamoyl)-methyl]-5-(2,4-dichloro-phenyl)-2-oxo-pyrrolidin-1-yl]-acetic acid
• CAS No.: 808189-02-8
• Molecular Formula: C₂₁H₁₉Cl₃N₂O₄
• Molecular Weight: 469.752

Synonyms:[(3R,5R)-3-[(3-Chloro-benzylcarbamoyl)-methyl]-5-(2,4-dichloro-phenyl)-2-oxo-pyrrolidin-1-yl]-acetic acid

Chemical Property of [(3R,5R)-3-[(3-Chloro-benzylcarbamoyl)-methyl]-5-(2,4-dichloro-phenyl)-2-oxo-pyrrolidin-1-yl]-acetic acid

Chemical Property:

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Technology Process of [(3R,5R)-3-[(3-Chloro-benzylcarbamoyl)-methyl]-5-(2,4-dichloro-phenyl)-2-oxo-pyrrolidin-1-yl]-acetic acid

There total 10 articles about [(3R,5R)-3-[(3-Chloro-benzylcarbamoyl)-methyl]-5-(2,4-dichloro-phenyl)-2-oxo-pyrrolidin-1-yl]-acetic 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: 80.0%

2-[1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-dichloro-phenyl)-2-oxo-pyrrolidin-3-yl]-N-(3-chloro-benzyl)-acetamide (808189-27-7) → [(3R,5R)-3-[(3-Chloro-benzylcarbamoyl)-methyl]-5-(2,4-dichloro-phenyl)-2-oxo-pyrrolidin-1-yl]-acetic acid (808189-02-8)

Guidance literature:

With jones reagent; In acetone;

DOI:10.1016/j.bmcl.2004.09.001

Reference yield:

4-(2,4-dichlorophenyl)-4-oxobutanoic acid (58457-57-1) → [(3R,5R)-3-[(3-Chloro-benzylcarbamoyl)-methyl]-5-(2,4-dichloro-phenyl)-2-oxo-pyrrolidin-1-yl]-acetic acid (808189-02-8)

Guidance literature:

Multi-step reaction with 8 steps

1.1: 100 percent / toluene / 16 h / Heating

2.1: 80 percent / TiCl₄; Et₃SiH / CH₂Cl₂ / 16 h / -78 - 20 °C

3.1: 95 percent / imidazole / dimethylformamide

4.1: LDA / tetrahydrofuran / -78 °C

4.2: 70 percent / tetrahydrofuran

5.1: ozone / CH₂Cl₂ / -78 °C

5.2: 90 percent / PS-PPh₃ / CH₂Cl₂

6.1: 90 percent / KMnO₄; NaH₂PO₄ / 2-methyl-propan-2-ol

7.1: 65 percent / EDCI; HOBt / H₂O

8.1: 80 percent / Jones reagent / acetone

With 1H-imidazole; triethylsilane; potassium permanganate; sodium dihydrogenphosphate; jones reagent; titanium tetrachloride; benzotriazol-1-ol; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;

DOI:10.1016/j.bmcl.2004.09.001

Reference yield:

1,3-Dichlorobenzene (541-73-1) → [(3R,5R)-3-[(3-Chloro-benzylcarbamoyl)-methyl]-5-(2,4-dichloro-phenyl)-2-oxo-pyrrolidin-1-yl]-acetic acid (808189-02-8)

Guidance literature:

Multi-step reaction with 10 steps

1.1: 80 percent / aluminum chloride / 0 - 80 °C

2.1: 90 percent / aq. LiOH / tetrahydrofuran

3.1: 100 percent / toluene / 16 h / Heating

4.1: 80 percent / TiCl₄; Et₃SiH / CH₂Cl₂ / 16 h / -78 - 20 °C

5.1: 95 percent / imidazole / dimethylformamide

6.1: LDA / tetrahydrofuran / -78 °C

6.2: 70 percent / tetrahydrofuran

7.1: ozone / CH₂Cl₂ / -78 °C

7.2: 90 percent / PS-PPh₃ / CH₂Cl₂

8.1: 90 percent / KMnO₄; NaH₂PO₄ / 2-methyl-propan-2-ol

9.1: 65 percent / EDCI; HOBt / H₂O

10.1: 80 percent / Jones reagent / acetone

With 1H-imidazole; triethylsilane; lithium hydroxide; potassium permanganate; sodium dihydrogenphosphate; aluminium trichloride; jones reagent; titanium tetrachloride; benzotriazol-1-ol; ozone; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; lithium diisopropyl amide; In tetrahydrofuran; dichloromethane; water; N,N-dimethyl-formamide; acetone; toluene; tert-butyl alcohol;

DOI:10.1016/j.bmcl.2004.09.001

upstream raw materials:

2-[1-[2-(tert-butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-dichloro-phenyl)-2-oxo-pyrrolidin-3-yl]-N-(3-chloro-benzyl)-acetamide

4-(2,4-dichlorophenyl)-4-oxobutanoic acid

1,3-Dichlorobenzene

5-(2,4-dichloro-phenyl)-1-(2-hydroxy-ethyl)-pyrrolidin-2-one

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