[(3R,5R)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-dichloro-phenyl)-2-oxo-pyrrolidin-3-yl]-acetic acid

Base Information

• Chemical Name: [(3R,5R)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-dichloro-phenyl)-2-oxo-pyrrolidin-3-yl]-acetic acid
• CAS No.: 808189-21-1
• Molecular Formula: C₂₀H₂₉Cl₂NO₄Si
• Molecular Weight: 446.446

Synonyms:[(3R,5R)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-dichloro-phenyl)-2-oxo-pyrrolidin-3-yl]-acetic acid

Chemical Property of [(3R,5R)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-dichloro-phenyl)-2-oxo-pyrrolidin-3-yl]-acetic acid

Chemical Property:

Purity/Quality:

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Technology Process of [(3R,5R)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-dichloro-phenyl)-2-oxo-pyrrolidin-3-yl]-acetic acid

There total 11 articles about [(3R,5R)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-dichloro-phenyl)-2-oxo-pyrrolidin-3-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: 90.0%

[(3R,5R)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-dichloro-phenyl)-2-oxo-pyrrolidin-3-yl]-acetaldehyde → [(3R,5R)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-dichloro-phenyl)-2-oxo-pyrrolidin-3-yl]-acetic acid (808189-21-1)

Guidance literature:

With potassium permanganate; sodium dihydrogenphosphate; In tert-butyl alcohol;

DOI:10.1016/j.bmcl.2004.09.001

Reference yield:

4-(2,4-dichlorophenyl)-4-oxobutanoic acid (58457-57-1) → [(3R,5R)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-dichloro-phenyl)-2-oxo-pyrrolidin-3-yl]-acetic acid (808189-21-1)

Guidance literature:

Multi-step reaction with 9 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 / SOCl₂ / tetrahydrofuran / 0 - 20 °C

4.1: 80 percent / NaOEt / ethanol / 45 °C

5.1: 85 percent / aq. HCl / tetrahydrofuran / Heating

6.1: 75 percent / KH / dimethylformamide / 1 h / 20 °C

7.1: LDA / tetrahydrofuran / -78 °C

7.2: 70 percent / tetrahydrofuran

8.1: ozone / CH₂Cl₂ / -78 °C

8.2: 90 percent / PS-PPh₃ / CH₂Cl₂

9.1: 90 percent / KMnO₄; NaH₂PO₄ / 2-methyl-propan-2-ol

With hydrogenchloride; triethylsilane; potassium permanganate; sodium dihydrogenphosphate; thionyl chloride; sodium ethanolate; titanium tetrachloride; potassium hydride; ozone; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1016/j.bmcl.2004.09.001

Reference yield:

1,3-Dichlorobenzene (541-73-1) → [(3R,5R)-1-[2-(tert-Butyl-dimethyl-silanyloxy)-ethyl]-5-(2,4-dichloro-phenyl)-2-oxo-pyrrolidin-3-yl]-acetic acid (808189-21-1)

Guidance literature:

Multi-step reaction with 11 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 / SOCl₂ / tetrahydrofuran / 0 - 20 °C

6.1: 80 percent / NaOEt / ethanol / 45 °C

7.1: 85 percent / aq. HCl / tetrahydrofuran / Heating

8.1: 75 percent / KH / dimethylformamide / 1 h / 20 °C

9.1: LDA / tetrahydrofuran / -78 °C

9.2: 70 percent / tetrahydrofuran

10.1: ozone / CH₂Cl₂ / -78 °C

10.2: 90 percent / PS-PPh₃ / CH₂Cl₂

11.1: 90 percent / KMnO₄; NaH₂PO₄ / 2-methyl-propan-2-ol

With hydrogenchloride; triethylsilane; lithium hydroxide; potassium permanganate; sodium dihydrogenphosphate; aluminium trichloride; thionyl chloride; sodium ethanolate; titanium tetrachloride; potassium hydride; ozone; lithium diisopropyl amide; In tetrahydrofuran; ethanol; dichloromethane; N,N-dimethyl-formamide; toluene; tert-butyl alcohol;

DOI:10.1016/j.bmcl.2004.09.001

upstream raw materials:

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

1,3-Dichlorobenzene

(R)-5-(2,4-Dichloro-phenyl)-pyrrolidin-2-one

(R)-5-(2,4-Dichloro-phenyl)-1-(1-phenyl-vinyl)-pyrrolidin-2-one

Downstream raw materials:

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

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