(5R,2S)-5-methyl-6-oxo-5,6-dihydro-4H-cyclopenta[b]thien-5-yl 2-amino-3-phenylpropanoate

Base Information

• Chemical Name: (5R,2S)-5-methyl-6-oxo-5,6-dihydro-4H-cyclopenta[b]thien-5-yl 2-amino-3-phenylpropanoate
• CAS No.: 1026640-09-4
• Molecular Formula: C₁₇H₁₇NO₃S
• Molecular Weight: 315.393
• Mol file: 1026640-09-4.mol

Synonyms:

Chemical Property of (5R,2S)-5-methyl-6-oxo-5,6-dihydro-4H-cyclopenta[b]thien-5-yl 2-amino-3-phenylpropanoate

Chemical Property:

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of (5R,2S)-5-methyl-6-oxo-5,6-dihydro-4H-cyclopenta[b]thien-5-yl 2-amino-3-phenylpropanoate

There total 5 articles about (5R,2S)-5-methyl-6-oxo-5,6-dihydro-4H-cyclopenta[b]thien-5-yl 2-amino-3-phenylpropanoate 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:

2-tert-butoxycarbonylamino-3-phenyl-propionic acid 5-methyl-6-oxo-5,6-dihydro-4H-cyclopenta[b]thiophen-5-yl ester → (5R,2S)-5-methyl-6-oxo-5,6-dihydro-4H-cyclopenta[b]thien-5-yl 2-amino-3-phenylpropanoate (1026640-09-4) + (5S,2S)-5-methyl-6-oxo-5,6-dihydro-4H-cyclopenta[b]thien-5-yl 2-amino-3-phenylpropanoate

Guidance literature:

With trifluoroacetic acid; In chloroform; at 20 ℃; for 3.5h;

DOI:10.1002/ejoc.200400351

Reference yield:

3-(3-thienyl)propanoic acid (16378-06-6) → (5R,2S)-5-methyl-6-oxo-5,6-dihydro-4H-cyclopenta[b]thien-5-yl 2-amino-3-phenylpropanoate (1026640-09-4)

Guidance literature:

Multi-step reaction with 5 steps

1.1: 54 percent / phosphorus pentoxide; methanesulfonic acid / 0.67 h / 20 °C

2.1: 81 percent / LDA / tetrahydrofuran / 12 h / 20 °C

3.1: KOH; iodobenzene diacetate / methanol / 24 h / 20 °C

3.2: 65 percent / HCl / ethanol / 2.5 h / 20 °C

4.1: 98 percent / N,N-dicyclohexylcarbodiimide; DMAP / CH₂Cl₂ / 8 h / 20 °C

5.1: 1.98 g / CF₃COOH / CHCl₃ / 3.5 h / 20 °C

With dmap; phosphorus pentaoxide; potassium hydroxide; methanesulfonic acid; [bis(acetoxy)iodo]benzene; dicyclohexyl-carbodiimide; trifluoroacetic acid; lithium diisopropyl amide; In tetrahydrofuran; methanol; dichloromethane; chloroform;

DOI:10.1002/ejoc.200400351

Reference yield:

4,5-dihydro-5-methyl-6H-cyclopentathiophen-6-one (13196-30-0) → (5R,2S)-5-methyl-6-oxo-5,6-dihydro-4H-cyclopenta[b]thien-5-yl 2-amino-3-phenylpropanoate (1026640-09-4)

Guidance literature:

Multi-step reaction with 3 steps

1.1: KOH; iodobenzene diacetate / methanol / 24 h / 20 °C

1.2: 65 percent / HCl / ethanol / 2.5 h / 20 °C

2.1: 98 percent / N,N-dicyclohexylcarbodiimide; DMAP / CH₂Cl₂ / 8 h / 20 °C

3.1: 1.98 g / CF₃COOH / CHCl₃ / 3.5 h / 20 °C

With dmap; potassium hydroxide; [bis(acetoxy)iodo]benzene; dicyclohexyl-carbodiimide; trifluoroacetic acid; In methanol; dichloromethane; chloroform;

DOI:10.1002/ejoc.200400351

upstream raw materials:

4,5-dihydro-5-methyl-6H-cyclopentathiophen-6-one

3-(3-thienyl)propanoic acid

4,5-dihydro-6H-cyclopenta[b]thiophen-6-one

(+/-) 5-hydroxy-5-methyl-4,5-dihydro-6H-cyclopenta[b]thiophen-6-one

Downstream raw materials:

(R,R)-N-(5-hydroxy-5-methyl-5,6-dihydro-4H-cyclopenta[b]thien-6-yl)benzamide

(R)-5-hydroxy-5-methyl-4,5-dihydro-6H-cyclopenta[b]thiophen-6-one O-methyloxime

Refernces