4-([2-((2R)-2-((1E,3S)-4-[3-(1,3-benzothiazol-2-yl)phenyl]-3-hydroxybut-1-enyl)-5-oxopyrrolidin-1-yl)ethyl]sulfanyl)butanoic acid

Base Information

• Chemical Name: 4-([2-((2R)-2-((1E,3S)-4-[3-(1,3-benzothiazol-2-yl)phenyl]-3-hydroxybut-1-enyl)-5-oxopyrrolidin-1-yl)ethyl]sulfanyl)butanoic acid
• CAS No.: 494224-12-3
• Molecular Formula: C₂₇H₃₀N₂O₄S₂
• Molecular Weight: 510.678

Synonyms:4-([2-((2R)-2-((1E,3S)-4-[3-(1,3-benzothiazol-2-yl)phenyl]-3-hydroxybut-1-enyl)-5-oxopyrrolidin-1-yl)ethyl]sulfanyl)butanoic acid

Chemical Property of 4-([2-((2R)-2-((1E,3S)-4-[3-(1,3-benzothiazol-2-yl)phenyl]-3-hydroxybut-1-enyl)-5-oxopyrrolidin-1-yl)ethyl]sulfanyl)butanoic acid

Chemical Property:

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Technology Process of 4-([2-((2R)-2-((1E,3S)-4-[3-(1,3-benzothiazol-2-yl)phenyl]-3-hydroxybut-1-enyl)-5-oxopyrrolidin-1-yl)ethyl]sulfanyl)butanoic acid

There total 10 articles about 4-([2-((2R)-2-((1E,3S)-4-[3-(1,3-benzothiazol-2-yl)phenyl]-3-hydroxybut-1-enyl)-5-oxopyrrolidin-1-yl)ethyl]sulfanyl)butanoic 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: 54.0%

n-butyl 4-((2-[(2R)-2-((1E,3S)-4-[3-(1,3-benzothiazol-2-yl)phenyl]-3-hydroxy-1-buten-1-yl)-5-oxo-1-pyrrolidinyl]ethyl)thio)butanoate (1380347-45-4) → 4-([2-((2R)-2-((1E,3S)-4-[3-(1,3-benzothiazol-2-yl)phenyl]-3-hydroxybut-1-enyl)-5-oxopyrrolidin-1-yl)ethyl]sulfanyl)butanoic acid (494224-12-3)

Guidance literature:

n-butyl 4-((2-[(2R)-2-((1E,3S)-4-[3-(1,3-benzothiazol-2-yl)phenyl]-3-hydroxy-1-buten-1-yl)-5-oxo-1-pyrrolidinyl]ethyl)thio)butanoate; With sodium hydroxide; In tetrahydrofuran; methanol; water; at 20 ℃; for 5h;

With hydrogenchloride; In tetrahydrofuran; methanol; water; Cooling;

DOI:10.1016/j.bmc.2012.04.008

Reference yield:

2-amino-benzenethiol (137-07-5) → 4-([2-((2R)-2-((1E,3S)-4-[3-(1,3-benzothiazol-2-yl)phenyl]-3-hydroxybut-1-enyl)-5-oxopyrrolidin-1-yl)ethyl]sulfanyl)butanoic acid (494224-12-3)

Guidance literature:

Multi-step reaction with 8 steps

1.1: polyphosphoric acid / 5 h / 200 °C / Inert atmosphere

2.1: sodium hydride / 1,3-dimethyl-2-imidazolidinone; mineral oil / 0.33 h / 0 - 20 °C / Inert atmosphere

2.2: 4 h / 120 °C / Inert atmosphere

3.1: sodium hydroxide / 1,2-dimethoxyethane; water / 2 h / 60 °C

3.2: 2 h / 60 °C

4.1: 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine / acetonitrile / 6 h / 20 °C / Inert atmosphere

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

5.2: 2 h / -78 °C / Inert atmosphere

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

6.2: 2 h / 0 °C / Inert atmosphere

7.1: 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

7.2: 0.08 h / 20 °C / Inert atmosphere

8.1: sodium hydroxide / tetrahydrofuran; methanol; water / 5 h / 20 °C

8.2: Cooling

With n-butyllithium; borane-THF; 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; 1,3-dimethyl-2-imidazolidinone; methanol; 1,2-dimethoxyethane; hexane; water; toluene; acetonitrile; mineral oil; 6.1: Horner-Wadsworth-Emmons olefination / 6.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.bmc.2012.04.008

Reference yield:

butyl 4-({2-[(2R)-2-formyl-5-oxo-1-pyrrolidinyl]ethyl}thio)butanoate (1365393-21-0) → 4-([2-((2R)-2-((1E,3S)-4-[3-(1,3-benzothiazol-2-yl)phenyl]-3-hydroxybut-1-enyl)-5-oxopyrrolidin-1-yl)ethyl]sulfanyl)butanoic acid (494224-12-3)

Guidance literature:

Multi-step reaction with 3 steps

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

1.2: 2 h / 0 °C / Inert atmosphere

2.1: 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

2.2: 0.08 h / 20 °C / Inert atmosphere

3.1: sodium hydroxide / tetrahydrofuran; methanol; water / 5 h / 20 °C

3.2: Cooling

With borane-THF; sodium hydride; sodium hydroxide; (3aR)-1-methyl-3,3-diphenyl-tetrahydro-pyrrolo[1,2-c][1,3,2]oxazaborole; In tetrahydrofuran; methanol; water; toluene; mineral oil; 1.1: Horner-Wadsworth-Emmons olefination / 1.2: Horner-Wadsworth-Emmons olefination;

DOI:10.1016/j.bmc.2012.04.008

upstream raw materials:

butyl 4-({2-[(2R)-2-formyl-5-oxo-1-pyrrolidinyl]ethyl}thio)butanoate

n-butyl 4-((2-[(2R)-2-((1E,3S)-4-[3-(1,3-benzothiazol-2-yl)phenyl]-3-hydroxy-1-buten-1-yl)-5-oxo-1-pyrrolidinyl]ethyl)thio)butanoate

N-methoxy-N-methyl-2-[3-(1,3-benzothiazol-2-yl)phenyl]acetamide

C₁₅H₁₁NO₂S

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