Spirapril hydrochloride

Base Information

• Chemical Name: Spirapril hydrochloride
• CAS No.: 94841-17-5
• Molecular Formula: C22H30N2O5S2.HCl
• Molecular Weight: 503.084
• European Community (EC) Number: 801-970-5
• UNII: OCC25LM897
• DSSTox Substance ID: DTXSID6044272
• Wikidata: Q27285573
• NCI Thesaurus Code: C66561
• ChEMBL ID: CHEMBL1200831
• Mol file: 94841-17-5.mol

Synonyms:Quadropril;Renormax;Renpress;SCH 33844;SCH-33844;spirapril;spirapril hydrochloride

Chemical Property of Spirapril hydrochloride

Chemical Property:

• Appearance/Colour: White Solid
• Vapor Pressure: 1.93E-20mmHg at 25°C
• Melting Point: 192-194°C
• Boiling Point: 697.8 °C at 760 mmHg
• Flash Point: 375.8 °C
• PSA: 146.54000
• LogP: 3.52160
• Storage Temp.: -20°C Freezer
• Solubility.: Very slightly soluble in water, soluble in methanol, slightly soluble in acetonitrile, practically insoluble in methylene chloride.
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 8
• Rotatable Bond Count: 10
• Exact Mass: 502.1362921
• Heavy Atom Count: 32
• Complexity: 650

Purity/Quality:

97% ^*data from raw suppliers

SpiraprilHydrochloride ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CCC1=CC=CC=C1)NC(C)C(=O)N2CC3(CC2C(=O)O)SCCS3.Cl
• Isomeric SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)N[C@@H](C)C(=O)N2CC3(C[C@H]2C(=O)O)SCCS3.Cl
• Description: Spirapril hydrochloride is a new ACE inhibitor introduced in Finland for the treatment of hypertension. Spirapril is orally active and rapidly absorbed and converted to the active diacid spiraprilat which produces a reduction in blood pressure similar to that seen with enalapril and captopril. Spirapril has been reported to be well tolerated and exhibits an apparently lower incidence of cough compared with other ACE inhibitors. The elimination of spirapril occurs via both renal and hepatic routes so that no dosage adjustment is required for patients with renal impairment. In patients with severe congestive heart failure, spirapril has demonstrated beneficial hemodynamic effects with a duration of action >24 hours.
• Uses: Angiotensin-converting enzyme (ACE) inhibior. Antihypertensive. Angiotensin-converting enzyme (ACE) inhibior. Antihypertensive

Technology Process of Spirapril hydrochloride

There total 9 articles about Spirapril 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:

spirapril (83647-97-6) → spirapril hydrochloride (94841-17-5)

Guidance literature:

With hydrogenchloride; In acetonitrile; at 5 ℃; for 10h;

DOI:10.1021/jm00127a033

Reference yield:

spirapril hydrochloride monohydrate → spirapril hydrochloride (94841-17-5)

Guidance literature:

In 1,4-dioxane; 1-pentyl acetate; Product distribution / selectivity; Heating / reflux;

Reference yield:

[1(S)-(ethoxycarbonyl)-3-phenylpropyl]-(S)-alanine (82717-96-2,122076-80-6) → spirapril hydrochloride (94841-17-5)

Guidance literature:

Multi-step reaction with 3 steps

1: 1->3-(dimethylamino)propyl>-3-ethylcarbodiimide hydrochloride / dimethylformamide / 18 h / Ambient temperature

2: 4.6 g / NEt₃ / dimethylformamide / Ambient temperature

3: 0.4 g / conc. aq. HCl / acetonitrile / 10 h / 5 °C

With hydrogenchloride; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; acetonitrile;

DOI:10.1021/jm00127a033

upstream raw materials:

spirapril

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

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

N-<(phenylmethoxy)carbonyl>-4-oxo-(S)-proline ethyl ester