Benzoic acid (S)-2-(imidazole-1-carbothioyloxy)-2-[1-(4-methoxy-phenyl)-5-oxo-pyrrolidin-3-yl]-ethyl ester

Base Information

• Chemical Name: Benzoic acid (S)-2-(imidazole-1-carbothioyloxy)-2-[1-(4-methoxy-phenyl)-5-oxo-pyrrolidin-3-yl]-ethyl ester
• CAS No.: 264903-82-4
• Molecular Formula: C₂₄H₂₃N₃O₅S
• Molecular Weight: 465.53

Synonyms:Benzoic acid (S)-2-(imidazole-1-carbothioyloxy)-2-[1-(4-methoxy-phenyl)-5-oxo-pyrrolidin-3-yl]-ethyl ester

Chemical Property of Benzoic acid (S)-2-(imidazole-1-carbothioyloxy)-2-[1-(4-methoxy-phenyl)-5-oxo-pyrrolidin-3-yl]-ethyl ester

Chemical Property:

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Technology Process of Benzoic acid (S)-2-(imidazole-1-carbothioyloxy)-2-[1-(4-methoxy-phenyl)-5-oxo-pyrrolidin-3-yl]-ethyl ester

There total 8 articles about Benzoic acid (S)-2-(imidazole-1-carbothioyloxy)-2-[1-(4-methoxy-phenyl)-5-oxo-pyrrolidin-3-yl]-ethyl ester 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: 86.0%

1,1'-Thiocarbonyldiimidazole (6160-65-2) + 4-[{(S)-2-benzoyloxy-1-hydroxy}ethyl]-1-(4-methoxyphenyl)-2-pyrrolidinone (264903-81-3) → Benzoic acid (S)-2-(imidazole-1-carbothioyloxy)-2-[1-(4-methoxy-phenyl)-5-oxo-pyrrolidin-3-yl]-ethyl ester (264903-82-4)

Guidance literature:

In 1,2-dichloro-ethane; for 60h; Heating;

DOI:10.3987/com-99-8805

Reference yield:

[2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-(4-methoxy-phenyl)-amine (264903-64-2) → Benzoic acid (S)-2-(imidazole-1-carbothioyloxy)-2-[1-(4-methoxy-phenyl)-5-oxo-pyrrolidin-3-yl]-ethyl ester (264903-82-4)

Guidance literature:

Multi-step reaction with 7 steps

1: 73 percent / DCC; DMAP / CH₂Cl₂ / 0 - 20 °C

2: 81 percent / KH in oil; methanesulfonyl azide / 1,2-dimethoxy-ethane / 4 h / 0 °C

3: rhodium(II) pivalate / benzene / 80 °C

4: 92 percent / aq. DMSO; NaCl / 28 h / 110 °C

5: 71 percent / aq. HCl; MeOH / 24 h / 20 °C

6: 97 percent / pyridine / CH₂Cl₂ / 18 h / 0 - 20 °C

7: 86 percent / 1,2-dichloro-ethane / 60 h / Heating

With pyridine; hydrogenchloride; methanol; dmap; rhodium(II) pivalate; potassium hydride; dimethyl sulfoxide; Methanesulfonyl azide; dicyclohexyl-carbodiimide; sodium chloride; In 1,2-dimethoxyethane; dichloromethane; 1,2-dichloro-ethane; benzene;

DOI:10.3987/com-99-8805

Reference yield:

(S)-N-(4-methoxyphenyl)-3,4-dihydroxy-3,4-O-isopropylidenebutanamide (264903-63-1) → Benzoic acid (S)-2-(imidazole-1-carbothioyloxy)-2-[1-(4-methoxy-phenyl)-5-oxo-pyrrolidin-3-yl]-ethyl ester (264903-82-4)

Guidance literature:

Multi-step reaction with 8 steps

1: 98 percent / LiAlH₄ / tetrahydrofuran / 17 h / Heating

2: 73 percent / DCC; DMAP / CH₂Cl₂ / 0 - 20 °C

3: 81 percent / KH in oil; methanesulfonyl azide / 1,2-dimethoxy-ethane / 4 h / 0 °C

4: rhodium(II) pivalate / benzene / 80 °C

5: 92 percent / aq. DMSO; NaCl / 28 h / 110 °C

6: 71 percent / aq. HCl; MeOH / 24 h / 20 °C

7: 97 percent / pyridine / CH₂Cl₂ / 18 h / 0 - 20 °C

8: 86 percent / 1,2-dichloro-ethane / 60 h / Heating

With pyridine; hydrogenchloride; methanol; dmap; lithium aluminium tetrahydride; rhodium(II) pivalate; potassium hydride; dimethyl sulfoxide; Methanesulfonyl azide; dicyclohexyl-carbodiimide; sodium chloride; In tetrahydrofuran; 1,2-dimethoxyethane; dichloromethane; 1,2-dichloro-ethane; benzene;

DOI:10.3987/com-99-8805

upstream raw materials:

1,1'-Thiocarbonyldiimidazole

4-[{(S)-2-benzoyloxy-1-hydroxy}ethyl]-1-(4-methoxyphenyl)-2-pyrrolidinone

[2-((S)-2,2-Dimethyl-[1,3]dioxolan-4-yl)-ethyl]-(4-methoxy-phenyl)-amine

(S)-N-(4-methoxyphenyl)-3,4-dihydroxy-3,4-O-isopropylidenebutanamide

Downstream raw materials:

4-[(2-benzoyloxy)ethyl]-1-(4-methoxyphenyl)-2-pyrrolidinone

benzoic acid 2-(5-oxo-pyrrolidin-3-yl)-ethyl ester

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