(2S,5R)-(+)-5-(2-hydroxyphenyl)-1-(3-mercaptopropionyl)-2-pyrrolidinecarboxylic acid

Base Information

• Chemical Name: (2S,5R)-(+)-5-(2-hydroxyphenyl)-1-(3-mercaptopropionyl)-2-pyrrolidinecarboxylic acid
• CAS No.: 79734-70-6
• Molecular Formula: C₁₄H₁₇NO₄S
• Molecular Weight: 295.359
• Mol file: 79734-70-6.mol

Synonyms:(2S,5R)-(+)-5-(2-hydroxyphenyl)-1-(3-mercaptopropionyl)-2-pyrrolidinecarboxylic acid

Chemical Property of (2S,5R)-(+)-5-(2-hydroxyphenyl)-1-(3-mercaptopropionyl)-2-pyrrolidinecarboxylic acid

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (2S,5R)-(+)-5-(2-hydroxyphenyl)-1-(3-mercaptopropionyl)-2-pyrrolidinecarboxylic acid

There total 11 articles about (2S,5R)-(+)-5-(2-hydroxyphenyl)-1-(3-mercaptopropionyl)-2-pyrrolidinecarboxylic 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: 85.0%

(+/-)-1-<3-(benzoylthio)propionyl>-5-(2-hydroxyphenyl)-2-pyrrolidinecarboxylic acid (75664-12-9,76016-11-0,76016-12-1,105560-85-8,105560-86-9,105560-87-0) → (+/-)-5-(2-hydroxyphenyl)-1-(3-mercaptopropionyl)-2-pyrrolidinecarboxylic acid (75664-11-8,76016-13-2,76016-14-3,79734-69-3,79734-70-6,105497-84-5,105497-85-6,105497-86-7)

Guidance literature:

With ammonium hydroxide; In water; for 1h; Ambient temperature;

DOI:10.1248/cpb.33.4836

Reference yield: 82.0%

(2S,5R)-(+)-1-<3-(benzoylthio)propionyl>-5-(2-hydroxyphenyl)-2-pyrrolidinecarboxylic acid (105560-85-8) → (2S,5R)-(+)-5-(2-hydroxyphenyl)-1-(3-mercaptopropionyl)-2-pyrrolidinecarboxylic acid (79734-70-6)

Guidance literature:

With ammonium hydroxide; In water; for 1h; Ambient temperature;

DOI:10.1248/cpb.33.4836

Reference yield:

o-hydroxyacetophenone (118-93-4,104809-67-8) → (+/-)-5-(2-hydroxyphenyl)-1-(3-mercaptopropionyl)-2-pyrrolidinecarboxylic acid (75664-11-8,76016-13-2,76016-14-3,79734-69-3,79734-70-6,105497-84-5,105497-85-6,105497-86-7)

Guidance literature:

Multi-step reaction with 8 steps

1: 46 percent / hydrogen chloride / ethanol / 6 h / Heating

2: NaOEt / ethanol / Ambient temperature

3: 1 h / Heating

4: 52 percent / 6N HCl / 4 h / Heating

5: 90 percent / 3N NaOH / H₂O / pH 4

6: H₂, 1N HCl / PtO₂ / H₂O

7: K₂CO₃ / H₂O / 1 h / under ice cooling

8: 85 percent / conc. ammonia / H₂O / 1 h / Ambient temperature

With hydrogenchloride; ammonium hydroxide; sodium hydroxide; hydrogen; sodium ethanolate; potassium carbonate; platinum(IV) oxide; In ethanol; water;

DOI:10.1248/cpb.33.4836

upstream raw materials:

(2S,5R)-(+)-1-<3-(benzoylthio)propionyl>-5-(2-hydroxyphenyl)-2-pyrrolidinecarboxylic acid

(2S,5R)-5-(2-Hydroxy-phenyl)-pyrrolidine-2-carboxylic acid; hydrochloride

Sodium; (S)-5-(2-hydroxy-phenyl)-3,4-dihydro-2H-pyrrole-2-carboxylate

(+/-)-1-<3-(benzoylthio)propionyl>-5-(2-hydroxyphenyl)-2-pyrrolidinecarboxylic acid

Downstream raw materials:

(2S,2'S,5R,5'R)-1,1'(3,3'-dithiodipropionyl)bis<5-(2-hydroxyphenyl)-2-pyrrolidinecarboxylic acid>

(2R,5R)-(+)-5-(2-hydroxyphenyl)-1-(3-mercaptopropionyl)-2-pyrrolidinecarboxylic acid

(2R,5R)-(+)-5-(2-acetoxyphenyl)-1-<3-(acetylthio)propionyl>-2-pyrrolidinecarboxylic acid

(2S,5R)-(+)-5-(2-acetoxyphenyl)-1-<3-(acetylthio)propionyl>-2-pyrrolidinecarboxylic acid

Refernces