(S)-6-((S)-4,4-difluoro-2-methoxycarbonyl-pyrrolidin-1-ylmethyl)-4-(4-fluoro-phenyl)-4-methyl-2-thiazol-2-yl-1,4-dihydro-pyrimidine-5-carboxylic acid methyl ester

Base Information

Chemical Name:(S)-6-((S)-4,4-difluoro-2-methoxycarbonyl-pyrrolidin-1-ylmethyl)-4-(4-fluoro-phenyl)-4-methyl-2-thiazol-2-yl-1,4-dihydro-pyrimidine-5-carboxylic acid methyl ester
CAS No.:1461665-87-1
Molecular Formula:C₂₃H₂₃F₃N₄O₄S
Molecular Weight:508.521
Hs Code.:

(S)-6-((S)-4,4-difluoro-2-methoxycarbonyl-pyrrolidin-1-ylmethyl)-4-(4-fluoro-phenyl)-4-methyl-2-thiazol-2-yl-1,4-dihydro-pyrimidine-5-carboxylic acid methyl ester

Synonyms:(S)-6-((S)-4,4-difluoro-2-methoxycarbonyl-pyrrolidin-1-ylmethyl)-4-(4-fluoro-phenyl)-4-methyl-2-thiazol-2-yl-1,4-dihydro-pyrimidine-5-carboxylic acid methyl ester

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Chemical Property of (S)-6-((S)-4,4-difluoro-2-methoxycarbonyl-pyrrolidin-1-ylmethyl)-4-(4-fluoro-phenyl)-4-methyl-2-thiazol-2-yl-1,4-dihydro-pyrimidine-5-carboxylic acid methyl ester

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Technology Process of (S)-6-((S)-4,4-difluoro-2-methoxycarbonyl-pyrrolidin-1-ylmethyl)-4-(4-fluoro-phenyl)-4-methyl-2-thiazol-2-yl-1,4-dihydro-pyrimidine-5-carboxylic acid methyl ester

There total 12 articles about (S)-6-((S)-4,4-difluoro-2-methoxycarbonyl-pyrrolidin-1-ylmethyl)-4-(4-fluoro-phenyl)-4-methyl-2-thiazol-2-yl-1,4-dihydro-pyrimidine-5-carboxylic acid methyl 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: 85.0%

: C₂₈H₃₁F₃N₄O₆S

: 1461665-87-1
(S)-6-((S)-4,4-difluoro-2-methoxycarbonyl-pyrrolidin-1-ylmethyl)-4-(4-fluoro-phenyl)-4-methyl-2-thiazol-2-yl-1,4-dihydro-pyrimidine-5-carboxylic acid methyl ester

Guidance literature:: With trifluoroacetic acid; In dichloromethane; at 20 ℃; for 2h;
DOI:10.1021/acs.jmedchem.6b00879

Reference yield:

: 105-45-3
acetoacetic acid methyl ester

: 1461665-87-1
(S)-6-((S)-4,4-difluoro-2-methoxycarbonyl-pyrrolidin-1-ylmethyl)-4-(4-fluoro-phenyl)-4-methyl-2-thiazol-2-yl-1,4-dihydro-pyrimidine-5-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 10 steps

1.1: piperidine; acetic acid / ethanol / 12 h / 20 °C

2.1: copper(l) iodide / tetrahydrofuran; diethyl ether / 1 h / 0 °C / Inert atmosphere

2.2: 1 h / -78 °C / Inert atmosphere

3.1: sodium hydride / tetrahydrofuran / 0.08 h / 20 °C / Inert atmosphere

3.2: 1 h / 20 °C / Inert atmosphere

4.1: dihydrogen peroxide; water / tetrahydrofuran; diethyl ether; dichloromethane / 1 h / 20 °C / Inert atmosphere

5.1: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one / 2 h / 120 °C

6.1: chiral column Daicel Chiralpak IC / Resolution of racemate

7.1: dmap / dichloromethane / 20 °C

8.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 2 h / 50 °C

9.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 40 °C

10.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

With piperidine; dmap; N-Bromosuccinimide; copper(l) iodide; 2,2'-azobis(isobutyronitrile); water; dihydrogen peroxide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; acetic acid; trifluoroacetic acid; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; tetrachloromethane; diethyl ether; ethanol; dichloromethane; N,N-dimethyl-formamide; 1.1: |Aldol Condensation / 2.2: |Michael Addition;
DOI:10.1021/acs.jmedchem.6b00879

Reference yield:

: C₁₃H₁₅FO₃

: 1461665-87-1
(S)-6-((S)-4,4-difluoro-2-methoxycarbonyl-pyrrolidin-1-ylmethyl)-4-(4-fluoro-phenyl)-4-methyl-2-thiazol-2-yl-1,4-dihydro-pyrimidine-5-carboxylic acid methyl ester

Guidance literature:: Multi-step reaction with 8 steps

1.1: sodium hydride / tetrahydrofuran / 0.08 h / 20 °C / Inert atmosphere

1.2: 1 h / 20 °C / Inert atmosphere

2.1: dihydrogen peroxide; water / tetrahydrofuran; diethyl ether; dichloromethane / 1 h / 20 °C / Inert atmosphere

3.1: sodium hydrogencarbonate / 1-methyl-pyrrolidin-2-one / 2 h / 120 °C

4.1: chiral column Daicel Chiralpak IC / Resolution of racemate

5.1: dmap / dichloromethane / 20 °C

6.1: N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile) / tetrachloromethane / 2 h / 50 °C

7.1: potassium carbonate / N,N-dimethyl-formamide / 3 h / 40 °C

8.1: trifluoroacetic acid / dichloromethane / 2 h / 20 °C

With dmap; N-Bromosuccinimide; 2,2'-azobis(isobutyronitrile); water; dihydrogen peroxide; sodium hydride; sodium hydrogencarbonate; potassium carbonate; trifluoroacetic acid; In tetrahydrofuran; 1-methyl-pyrrolidin-2-one; tetrachloromethane; diethyl ether; dichloromethane; N,N-dimethyl-formamide;
DOI:10.1021/acs.jmedchem.6b00879