(2S,3R)-3-(3-carboxy-5-(pyrimidin-5-yl)phenyl)pyrrolidine-2-carboxylic acid hydrochloride

Base Information

Chemical Name:(2S,3R)-3-(3-carboxy-5-(pyrimidin-5-yl)phenyl)pyrrolidine-2-carboxylic acid hydrochloride
CAS No.:1622235-94-2
Molecular Formula:C₁₆H₁₅N₃O₄*ClH
Molecular Weight:349.774
Hs Code.:

Synonyms:

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Chemical Property of (2S,3R)-3-(3-carboxy-5-(pyrimidin-5-yl)phenyl)pyrrolidine-2-carboxylic acid hydrochloride

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Technology Process of (2S,3R)-3-(3-carboxy-5-(pyrimidin-5-yl)phenyl)pyrrolidine-2-carboxylic acid hydrochloride

There total 11 articles about (2S,3R)-3-(3-carboxy-5-(pyrimidin-5-yl)phenyl)pyrrolidine-2-carboxylic acid hydrochloride 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:

: (2S,3R)-1-(tert-butoxycarbonyl)-3-(3-carboxy-5-(pyrimidin-5-yl)phenyl)pyrrolidine-2-carboxylic acid

: 1622235-94-2
(2S,3R)-3-(3-carboxy-5-(pyrimidin-5-yl)phenyl)pyrrolidine-2-carboxylic acid hydrochloride

Guidance literature:: (2S,3R)-1-(tert-butoxycarbonyl)-3-(3-carboxy-5-(pyrimidin-5-yl)phenyl)pyrrolidine-2-carboxylic acid; With trifluoroacetic acid; In dichloromethane; at 0 - 20 ℃; for 2.5h;

With hydrogenchloride; In water;
DOI:10.1021/acschemneuro.0c00003

Reference yield:

: 913835-73-1
3-bromo-5-carboxyphenylboronic acid

: 1622235-94-2
(2S,3R)-3-(3-carboxy-5-(pyrimidin-5-yl)phenyl)pyrrolidine-2-carboxylic acid hydrochloride

Guidance literature:: Multi-step reaction with 10 steps

1: sulfuric acid / 20 h / Reflux

2: diethyl ether / 1.5 h / 20 °C

3: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C

4: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C

5: chloro(1,5-cyclooctadiene)rhodium(I) dimer; caesium carbonate; water / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

6: boron trichloride methyl sulfide complex / tetrahydrofuran / 2 h / Reflux

7: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 20 °C

8: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane / 4 h / 95 °C / Inert atmosphere; Sealed tube

9: sodium periodate; ruthenium(III) trichloride hydrate / ethyl acetate; acetonitrile; water / 2 h / 0 °C

10: trifluoroacetic acid / dichloromethane / 2.5 h / 0 - 20 °C

With 1H-imidazole; dmap; sodium periodate; lithium aluminium tetrahydride; chloro(1,5-cyclooctadiene)rhodium(I) dimer; tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron trichloride methyl sulfide complex; ruthenium(III) trichloride hydrate; sulfuric acid; tetrabutyl ammonium fluoride; water; sodium carbonate; caesium carbonate; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 8: |Suzuki Coupling;
DOI:10.1021/acschemneuro.0c00003

Reference yield:

: 913835-87-7
(3-bromo-5-(methoxycarbonyl)phenyl)boronic acid

: 1622235-94-2
(2S,3R)-3-(3-carboxy-5-(pyrimidin-5-yl)phenyl)pyrrolidine-2-carboxylic acid hydrochloride

Guidance literature:: Multi-step reaction with 9 steps

1: diethyl ether / 1.5 h / 20 °C

2: lithium aluminium tetrahydride / tetrahydrofuran / 14 h / 0 - 20 °C

3: 1H-imidazole; dmap / N,N-dimethyl-formamide / 21 h / 20 °C

4: chloro(1,5-cyclooctadiene)rhodium(I) dimer; caesium carbonate; water / tetrahydrofuran / 24 h / 20 °C / Inert atmosphere

5: boron trichloride methyl sulfide complex / tetrahydrofuran / 2 h / Reflux

6: tetrabutyl ammonium fluoride / tetrahydrofuran / 7 h / 20 °C

7: tetrakis(triphenylphosphine) palladium⁽⁰⁾; sodium carbonate / 1,4-dioxane / 4 h / 95 °C / Inert atmosphere; Sealed tube

8: sodium periodate; ruthenium(III) trichloride hydrate / ethyl acetate; acetonitrile; water / 2 h / 0 °C

9: trifluoroacetic acid / dichloromethane / 2.5 h / 0 - 20 °C

With 1H-imidazole; dmap; sodium periodate; lithium aluminium tetrahydride; chloro(1,5-cyclooctadiene)rhodium(I) dimer; tetrakis(triphenylphosphine) palladium⁽⁰⁾; boron trichloride methyl sulfide complex; ruthenium(III) trichloride hydrate; tetrabutyl ammonium fluoride; water; sodium carbonate; caesium carbonate; trifluoroacetic acid; In tetrahydrofuran; 1,4-dioxane; diethyl ether; dichloromethane; water; ethyl acetate; N,N-dimethyl-formamide; acetonitrile; 7: |Suzuki Coupling;
DOI:10.1021/acschemneuro.0c00003