(2S,4S)-1-(2,2-diphenylacetyl)-4-(5-phenyloxazol-2-yl)pyrrolidine-2-carboxylic acid

Base Information

• Chemical Name: (2S,4S)-1-(2,2-diphenylacetyl)-4-(5-phenyloxazol-2-yl)pyrrolidine-2-carboxylic acid
• CAS No.: 1446653-58-2
• Molecular Formula: C₂₈H₂₄N₂O₄
• Molecular Weight: 452.51
• Mol file: 1446653-58-2.mol

Synonyms:(2S,4S)-1-(2,2-diphenylacetyl)-4-(5-phenyloxazol-2-yl)pyrrolidine-2-carboxylic acid

Chemical Property of (2S,4S)-1-(2,2-diphenylacetyl)-4-(5-phenyloxazol-2-yl)pyrrolidine-2-carboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,4S)-1-(2,2-diphenylacetyl)-4-(5-phenyloxazol-2-yl)pyrrolidine-2-carboxylic acid

There total 11 articles about (2S,4S)-1-(2,2-diphenylacetyl)-4-(5-phenyloxazol-2-yl)pyrrolidine-2-carboxylic 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: 55.0%

C29H26N2O4 (1446655-32-8) → (2S,4S)-1-(2,2-diphenylacetyl)-4-(5-phenyloxazol-2-yl)pyrrolidine-2-carboxylic acid (1446653-58-2)

Guidance literature:

C₂₉H₂₆N₂O₄; With lithium hydroxide monohydrate; In tetrahydrofuran; water; at 20 ℃; pH=4 - 5;

With hydrogenchloride; In water;

Reference yield:

4R-4-hydroxyproline (51-35-4,30724-02-8) → (2S,4S)-1-(2,2-diphenylacetyl)-4-(5-phenyloxazol-2-yl)pyrrolidine-2-carboxylic acid (1446653-58-2)

Guidance literature:

Multi-step reaction with 11 steps

1.1: thionyl chloride / Reflux

2.1: potassium carbonate / water; diethyl ether / 2 h / 0 - 20 °C

3.1: triethylamine / dichloromethane / 20 - 40 °C

4.1: cesium fluoride / N,N-dimethyl-formamide / 40 h / 60 °C

5.1: 1 h / 0 - 20 °C

5.2: 48 h / 20 °C

6.1: sodium hydroxide / tetrahydrofuran / 1.5 h / 0 - 20 °C

6.2: pH 3 - 4

7.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 20 °C

7.2: 20 °C

8.1: pyridine; trifluoroacetic anhydride / dichloromethane / 3.25 h / 0 - 20 °C

9.1: 10 wt% Pd(OH)2 on carbon; (2S,4R)-1-(2,2-diphenylacetyl)-4-(3-phenylpropoxy)pyrrolidine-2-carboxylic acid / methanol / 2 h / 760.05 Torr

10.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 20 °C

11.1: lithium hydroxide monohydrate / water; tetrahydrofuran / 20 °C / pH 4 - 5

With pyridine; thionyl chloride; lithium hydroxide monohydrate; 10 wt% Pd(OH)2 on carbon; (2S,4R)-1-(2,2-diphenylacetyl)-4-(3-phenylpropoxy)pyrrolidine-2-carboxylic acid; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; cesium fluoride; HATU; trifluoroacetic anhydride; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

Reference yield:

trans-4-hydroxy-L-proline ethyl ester hydrochloride (33996-30-4) → (2S,4S)-1-(2,2-diphenylacetyl)-4-(5-phenyloxazol-2-yl)pyrrolidine-2-carboxylic acid (1446653-58-2)

Guidance literature:

Multi-step reaction with 10 steps

1.1: potassium carbonate / water; diethyl ether / 2 h / 0 - 20 °C

2.1: triethylamine / dichloromethane / 20 - 40 °C

3.1: cesium fluoride / N,N-dimethyl-formamide / 40 h / 60 °C

4.1: 1 h / 0 - 20 °C

4.2: 48 h / 20 °C

5.1: sodium hydroxide / tetrahydrofuran / 1.5 h / 0 - 20 °C

5.2: pH 3 - 4

6.1: N-ethyl-N,N-diisopropylamine; HATU / N,N-dimethyl-formamide / 0.5 h / 20 °C

6.2: 20 °C

7.1: pyridine; trifluoroacetic anhydride / dichloromethane / 3.25 h / 0 - 20 °C

8.1: 10 wt% Pd(OH)2 on carbon; (2S,4R)-1-(2,2-diphenylacetyl)-4-(3-phenylpropoxy)pyrrolidine-2-carboxylic acid / methanol / 2 h / 760.05 Torr

9.1: N-ethyl-N,N-diisopropylamine / dichloromethane / 0.5 h / 0 - 20 °C

10.1: lithium hydroxide monohydrate / water; tetrahydrofuran / 20 °C / pH 4 - 5

With pyridine; lithium hydroxide monohydrate; 10 wt% Pd(OH)2 on carbon; (2S,4R)-1-(2,2-diphenylacetyl)-4-(3-phenylpropoxy)pyrrolidine-2-carboxylic acid; potassium carbonate; triethylamine; N-ethyl-N,N-diisopropylamine; cesium fluoride; HATU; trifluoroacetic anhydride; sodium hydroxide; In tetrahydrofuran; methanol; diethyl ether; dichloromethane; water; N,N-dimethyl-formamide;

upstream raw materials:

4R-4-hydroxyproline

trans-4-hydroxy-L-proline ethyl ester hydrochloride

(2S,4R)-ethyl N¹-(benzyloxycarbonyl)-4-hydroxypyrrolidine-2-carboxylate

1-benzyl 2-ethyl(2S,4R)-4-[[(4-methylbenzene)sulfonyl]oxy]pyrrolidine-1,2-dicarboxylate

Refernces