CID 6992028

Base Information

• Chemical Name: CID 6992028
• CAS No.: 87333-19-5
• Molecular Formula: C23H32N2O5
• Molecular Weight: 416.517
• Hs Code.: 2933995300
• Pharos Ligand ID: 8CN6GB1S8ZV9
• Mol file: 87333-19-5.mol

Synonyms:

Chemical Property of CID 6992028

Chemical Property:

• Appearance/Colour: White solid
• Melting Point: 106-108 °C
• Boiling Point: 616.2 °C at 760 mmHg
• PKA: pKa 3.30±0.01(H2O t = 25.0 I = 0.15 (KCl)) (Uncertain);5.75±0.00(H2O t = 25.0 I = 0.15 (KCl)) (Uncertain)
• Flash Point: 326.4 °C
• PSA: 95.94000
• Density: 1.2 g/cm³
• LogP: 2.71200
• Storage Temp.: 2-8°C
• Solubility.: DMSO: ~18mg/mL
• XLogP3: 2.1
• Hydrogen Bond Donor Count: 1
• Hydrogen Bond Acceptor Count: 5
• Rotatable Bond Count: 9
• Exact Mass: 416.23112213
• Heavy Atom Count: 30
• Complexity: 613

Purity/Quality:

99%, ^*data from raw suppliers

Ramipril ^*data from reagent suppliers

Safty Information:

• Pictogram(s): Xi
• Hazard Codes: Xi
• Statements: 36/38
• Safety Statements: 26-37/39

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCOC(=O)C(CCC1=CC=CC=C1)[NH2+]C(C)C(=O)N2C3CCCC3CC2C(=O)[O-]
• Isomeric SMILES: CCOC(=O)[C@H](CCC1=CC=CC=C1)[NH2+][C@@H](C)C(=O)N2[C@H]3CCC[C@H]3C[C@H]2C(=O)[O-]
• Description: Ramipril (brand name: Altace) is a kind of prodrug which is capable of inhibiting the angiotensin-converting enzyme (ACE) which converting angiotensin I to angiotensin II. It is metabolized to ramiprilat in the liver which exerts the effect of ACE inhibition. It is used for the treatment of hypertension, congestive heart failure and nephropathy. It can also be used for the prevention of heart attack, stroke and cardiovascular death. It can also be used for the treatment of kidney damage due to diabetes with protein-containing urine. Ramiprilat, is the competitive inhibitor of ATI for binding to ACE, further inhibiting the enzymatic proteolysis of ATI to ATII, alleviating the effect of ATII on blood pressure. Ramipril, a prodrug of ramiprilat, is a long-acting, tissue-specific and non-sulfhydryl ACE inhibitor useful in the treatment of mild to moderate hypertension. In animal studies ramipril exerted cardioprotective effects resembling those of bradykinin in cardiac reperfusion injuries. Ramipril is also reportedly useful in congestive heart failure.
• Uses: An antihypertensive. An angiotensin converting enzyme (ACE) inhibitor, converted to active, diacid metabolite An inhibitor of the angiotensin- coverting enzyme (ACE) Angiotensin-converting enzyme (ACE) removes the C-terminal dipeptide from angiotensin I to form angiotensin II, a powerful vasoconstrictor. ACE is a key regulator of the renin-angiotensin system and an important drug target for the treatment of hypertension, congestive heart failure, and heart attacks, and also in preventing renal and retinal complications in diabetes. Ramipril is a second generation ACE inhibitor (IC50 = 4 nM) that acts as a prodrug, which is hydrolyzed in vivo to the active metabolite ramiprilat. The antihypertensive and cardioprotective efficacy of ramipril has been demonstrated in large-scale noncomparative studies and clinical trials.[Cayman Chemical]
• Clinical Use: Angiotensin-converting enzyme inhibitor: Hypertension Secondary prevention of myocardial infarction (MI), stroke or cardiovascular death Heart failure Diabetic nephropathy
• Drug interactions: Potentially hazardous interactions with other drugs Anaesthetics: enhanced hypotensive effect. Analgesics: antagonism of hypotensive effect and increased risk of renal impairment with NSAIDs; hyperkalaemia with ketorolac and other NSAIDs. Antihypertensives: increased risk of hyperkalaemia, hypotension and renal failure with ARB’S and aliskiren. Bee venom extract: possible severe anaphylactoid reactions when used together. Ciclosporin: increased risk of hyperkalaemia and nephrotoxicity. Cytotoxics: increased risk of angioedema with everolimus. Diuretics: enhanced hypotensive effect; hyperkalaemia with potassium-sparing diuretics. ESAs: increased risk of hyperkalaemia; antagonism of hypotensive effect. Gold: flushing and hypotension with sodium aurothiomalate. Lithium: reduced excretion (possibility of enhanced lithium toxicity). Potassium salts: increased risk of hyperkalaemia. Tacrolimus: increased risk of hyperkalaemia and nephrotoxicity

Technology Process of CID 6992028

There total 27 articles about CID 6992028 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: 94.0%

(2S,3aS,6aS)-1-[(S)-2-[[(S)-1-(ethoxycarbonyl)-3-phenylpropyl]-amino]propanoyl]octahydrocyclopenta[b]pyrrole-2-carboxylic acid monohydrate → Ramipril (87333-19-5,104195-90-6,1246253-05-3)

Guidance literature:

at 40 ℃; for 10 - 12h; under 2 Torr; Product distribution / selectivity;

Reference yield: 88.0%

N-[(S)-1-carbethoxy-3-phenyl-propyl]-S-alaninoyl chloride hydrochloride (114192-42-6) + (2S,3aS,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid (109428-53-7,411232-21-8,726691-28-7) → Ramipril (87333-19-5,104195-90-6,1246253-05-3)

Guidance literature:

(2S,3aS,6aS)-1-(tert-butoxycarbonyl)octahydrocyclopenta[b]pyrrole-2-carboxylic acid; With sodium ethanolate; triethylamine; In ethanol; at -40 ℃;

N-[(S)-1-carbethoxy-3-phenyl-propyl]-S-alaninoyl chloride hydrochloride; In ethanol; dichloromethane; at -50 - 20 ℃; for 1.08333h;

With hydrogenchloride; In water; pH=4.2; Acidic aqueous solution;

Reference yield: 74.0%

C8H13NO2*(x)ClH + N-[1-(S)-ethoxycarbonyl-3-phenylpropyl]-L-alanine N-carboxyanhydride (84793-24-8) → Ramipril (87333-19-5,104195-90-6,1246253-05-3)

Guidance literature:

With sodium hydroxide; In water; at 10 - 15 ℃; pH=8.5 - 9.5;

upstream raw materials:

2--L-alanyl>-(1S,3S,5S)-2-azabicyclo<3.3.0>octane-3-carboxylic acid benzylester

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

N-[1(S)-ethoxycarbonyl-3-phenylpropyl]-(S)-alanine-2'-benzothiazolylthio ester

ethyl (E)-4-oxo-4-phenyl-2-butenoate

Downstream raw materials:

ramiprilate

ramipril tris(hydroxymethyl)aminomethane salt

ramipril-ammonia

ramipril tert-butylamine salt

Refernces

• 1、 -. "A METHOD FOR PREPARING RAMIPRIL". . . Retrieved 2015/04/15.
• 2、 -. "COMPOSITIONS AND METHODS FOR DIAGNOSING AND TREATING SALT SENSITIVITY OF BLOOD PRESSURE". . . Retrieved 2015/02/05.