7-((2R)-2-{(1E,3S)-3-hydroxy-4-[3-(2,2,2-trifluoroethoxymethyl)phenyl]-1-buten-1-yl}-5-oxo-1-pyrrolidinyl)heptanoic acid

Base Information

• Chemical Name: 7-((2R)-2-{(1E,3S)-3-hydroxy-4-[3-(2,2,2-trifluoroethoxymethyl)phenyl]-1-buten-1-yl}-5-oxo-1-pyrrolidinyl)heptanoic acid
• CAS No.: 494221-69-1
• Molecular Formula: C₂₄H₃₂F₃NO₅
• Molecular Weight: 471.517

Synonyms:7-((2R)-2-{(1E,3S)-3-hydroxy-4-[3-(2,2,2-trifluoroethoxymethyl)phenyl]-1-buten-1-yl}-5-oxo-1-pyrrolidinyl)heptanoic acid

Chemical Property of 7-((2R)-2-{(1E,3S)-3-hydroxy-4-[3-(2,2,2-trifluoroethoxymethyl)phenyl]-1-buten-1-yl}-5-oxo-1-pyrrolidinyl)heptanoic acid

Chemical Property:

Purity/Quality:

Safty Information:

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Technology Process of 7-((2R)-2-{(1E,3S)-3-hydroxy-4-[3-(2,2,2-trifluoroethoxymethyl)phenyl]-1-buten-1-yl}-5-oxo-1-pyrrolidinyl)heptanoic acid

There total 11 articles about 7-((2R)-2-{(1E,3S)-3-hydroxy-4-[3-(2,2,2-trifluoroethoxymethyl)phenyl]-1-buten-1-yl}-5-oxo-1-pyrrolidinyl)heptanoic 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: 100.0%

ethyl 7-[(2R)-2-{(1E,3S)-3-hydroxy-4-[3-(2,2,2-trifluoroethoxymethyl)phenyl]-1-buten-1-yl}-5-oxo-1-pyrrolidinyl]heptanoate (1365391-90-7) → 7-((2R)-2-{(1E,3S)-3-hydroxy-4-[3-(2,2,2-trifluoroethoxymethyl)phenyl]-1-buten-1-yl}-5-oxo-1-pyrrolidinyl)heptanoic acid (494221-69-1)

Guidance literature:

With water; sodium hydroxide; In 1,2-dimethoxyethane; at 20 ℃; for 10h;

DOI:10.1248/cpb.59.1523

Reference yield:

C12H12F6O2 → 7-((2R)-2-{(1E,3S)-3-hydroxy-4-[3-(2,2,2-trifluoroethoxymethyl)phenyl]-1-buten-1-yl}-5-oxo-1-pyrrolidinyl)heptanoic acid (494221-69-1)

Guidance literature:

Multi-step reaction with 7 steps

1.1: bis-triphenylphosphine-palladium(II) chloride; potassium carbonate / tetrahydrofuran / 3 h / 20 °C / Inert atmosphere

2.1: water; sodium hydroxide / methanol / 1 h / 20 °C

3.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / acetonitrile / 1 h / 20 °C / Inert atmosphere

4.1: n-butyllithium / hexane; toluene / 1 h / -78 °C / Inert atmosphere

4.2: 2 h / -78 °C / Inert atmosphere

5.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 - 20 °C / Inert atmosphere

5.2: 2 h / 0 °C / Inert atmosphere

6.1: borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.08 h / 20 °C / Inert atmosphere

7.1: water; sodium hydroxide / 1,2-dimethoxyethane / 10 h / 20 °C

With bis-triphenylphosphine-palladium(II) chloride; n-butyllithium; borane-THF; water; sodium hydride; potassium carbonate; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; toluene; acetonitrile; mineral oil; 5.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1248/cpb.59.1523

Reference yield:

methyl {3-[(2,2,2-trifluoroethoxy)methyl]phenyl}acetate (1365392-91-1) → 7-((2R)-2-{(1E,3S)-3-hydroxy-4-[3-(2,2,2-trifluoroethoxymethyl)phenyl]-1-buten-1-yl}-5-oxo-1-pyrrolidinyl)heptanoic acid (494221-69-1)

Guidance literature:

Multi-step reaction with 6 steps

1.1: water; sodium hydroxide / methanol / 1 h / 20 °C

2.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / acetonitrile / 1 h / 20 °C / Inert atmosphere

3.1: n-butyllithium / hexane; toluene / 1 h / -78 °C / Inert atmosphere

3.2: 2 h / -78 °C / Inert atmosphere

4.1: sodium hydride / tetrahydrofuran; mineral oil / 1.5 h / 0 - 20 °C / Inert atmosphere

4.2: 2 h / 0 °C / Inert atmosphere

5.1: borane-THF; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole / tetrahydrofuran; toluene / 1.08 h / 20 °C / Inert atmosphere

6.1: water; sodium hydroxide / 1,2-dimethoxyethane / 10 h / 20 °C

With n-butyllithium; borane-THF; water; sodium hydride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; sodium hydroxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; methanol; 1,2-dimethoxyethane; hexane; toluene; acetonitrile; mineral oil; 4.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1248/cpb.59.1523

upstream raw materials:

methyl {3-[(2,2,2-trifluoroethoxy)methyl]phenyl}acetate

dimethyl [3-[3-(2,2,2-trifluoroethoxymethyl)phenyl]-2-oxopropane]phosphonate

ethyl 7-[(2R)-2-{(1E,3S)-3-hydroxy-4-[3-(2,2,2-trifluoroethoxymethyl)phenyl]-1-buten-1-yl}-5-oxo-1-pyrrolidinyl]heptanoate

ethyl (R)-7-(2-formyl-5-oxopyrrolidin-1-yl)heptanoate

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