Spiraprilat

Base Information

• Chemical Name: Spiraprilat
• CAS No.: 83507-88-4
• Molecular Formula: C₂₀H₂₆N₂O₅S₂
• Molecular Weight: 438.569
• Mol file: 83507-88-4.mol

Synonyms:

Chemical Property of Spiraprilat

Chemical Property:

• Vapor Pressure: 3.36E-21mmHg at 25°C
• Boiling Point: 710.7°C at 760 mmHg
• PKA: 2.19±0.10(Predicted)
• Flash Point: 383.6°C
• PSA: 157.54000
• Density: 1.41g/cm³
• LogP: 2.24110

Purity/Quality:

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

Useful:

Technology Process of Spiraprilat

There total 23 articles about Spiraprilat 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:

1-benzyloxycarbonyl-4-keto-L-proline (64187-47-9) → Spiraprilat (83602-05-5,83507-88-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 6.8 g / SOCl₂ / 20 h / Heating

2: 3.86 g / p-toluenesulfonic acid / acetic acid / 44 h / Heating

3: 6.3 g / 20percent HBr/glacial acetic acid / 2 h / Ambient temperature

4: 3.64 g / 2.5 N aq. NaOH / methanol / 18 h / Ambient temperature

5: 1.) N,N-disuccinimidyl carbonate, pyridine, 2.) NEt₃ / 1.) CH₃CN, RT, 44 h, 2.) CH₃CN, H₂O, RT

6: 6.22 g / 2.5 N aq. NaOH / methanol / 20 h / Ambient temperature

With pyridine; sodium hydroxide; thionyl chloride; di(succinimido) carbonate; hydrogen bromide; toluene-4-sulfonic acid; acetic acid; triethylamine; In methanol; acetic acid;

DOI:10.1021/jm00127a033

Reference yield:

1-benzyloxycarbonyl-4-keto-L-proline (64187-47-9) → 7--(S)-alanyl>-1,4-dithia-7-azaspiro<4.4>nonane-8(S)-carboxylic acid (83507-88-4)

Guidance literature:

Multi-step reaction with 6 steps

1: 6.8 g / SOCl₂ / 20 h / Heating

2: 3.86 g / p-toluenesulfonic acid / acetic acid / 44 h / Heating

3: 6.3 g / 20percent HBr/glacial acetic acid / 2 h / Ambient temperature

4: 3.64 g / 2.5 N aq. NaOH / methanol / 18 h / Ambient temperature

5: 1.) N,N-disuccinimidyl carbonate, pyridine, 2.) NEt₃ / 1.) CH₃CN, RT, 2.) CH₃CN, H₂O, RT

6: 0.67 g / 2.5 N aq. NaOH / methanol / 20 h / Ambient temperature

With pyridine; sodium hydroxide; thionyl chloride; di(succinimido) carbonate; hydrogen bromide; toluene-4-sulfonic acid; acetic acid; triethylamine; In methanol; acetic acid;

DOI:10.1021/jm00127a033

Reference yield:

(S,S,S)-7-[2-[(1-Ethoxycarbonyl-3-phenylpropyl)amino]-1-oxopropyl]-1,4-dithia-7-azaspiro[4.4]-nonane-8-carboxylic acid,methyl ester → (S,S,S)-7-[2-[(1-carboxy-3-phenylpropyl)amino]-1-oxopropyl]-1,4-dithia-7-azaspiro[4.4]nonane-8-carboxylic acid (83507-88-4)

Guidance literature:

With sodium; In ethanol;

upstream raw materials:

spirapril

(S)-7-[(S)-2-((S)-1-Ethoxycarbonyl-3-phenyl-propylamino)-propionyl]-1,4-dithia-7-aza-spiro[4.4]nonane-8-carboxylic acid methyl ester

[1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine

1,4-dithia-7-azaspiro<4.4>nonane-8(S)-carboxylic acid