Delapril diacid

Base Information

• Chemical Name: Delapril diacid
• CAS No.: 83398-08-7
• Molecular Formula: C24H28N2O5
• Molecular Weight: 424.497
• UNII: 50A464U6E7
• DSSTox Substance ID: DTXSID10232315
• Nikkaji Number: J509.679K
• Wikidata: Q27260781
• Mol file: 83398-08-7.mol

Synonyms:Delapril diacid;83398-08-7;Delaprilat;UNII-50A464U6E7;50A464U6E7;(2S)-2-[[(2S)-1-[carboxymethyl(2,3-dihydro-1H-inden-2-yl)amino]-1-oxopropan-2-yl]amino]-4-phenylbutanoic acid;(2S)-2-[[(1S)-1-(carboxymethyl-(2,3-dihydro-1H-inden-2-yl)carbamoyl)ethyl]amino]-4-phenyl-butanoic acid;Glycine, N-((1S)-1-carboxy-3-phenylpropyl)-L-alanyl-N-(2,3-dihydro-1H-inden-2-yl)-;N-[(1S)-1-Carboxy-3-phenylpropyl]-L-alanyl-N-(2,3-dihydro-1H-inden-2-yl)glycine;SCHEMBL7427496;DTXSID10232315;C21575;Q27260781;[N-(Indan-2-yl)-N-[(S)-1-[(S)-1-carboxy-3-phenylpropylamino]ethylcarbonyl]amino]acetic acid;GLYCINE, N-(N-(1-CARBOXY-3-PHENYLPROPYL)-L-ALANYL)-N-(2,3-DIHYDRO-1H-INDEN-2-YL)-, (S)-

Chemical Property of Delapril diacid

Chemical Property:

• Vapor Pressure: 1.14E-18mmHg at 25°C
• Boiling Point: 666.4°C at 760 mmHg
• Flash Point: 356.8°C
• PSA: 106.94000
• Density: 1.29g/cm³
• LogP: 2.52200
• XLogP3: 1
• Hydrogen Bond Donor Count: 3
• Hydrogen Bond Acceptor Count: 6
• Rotatable Bond Count: 10
• Exact Mass: 424.19982200
• Heavy Atom Count: 31
• Complexity: 620

Purity/Quality:

99% ^*data from raw suppliers

N-[(1S)-1-Carboxy-3-phenylpropyl]-L-alanyl-N-(2,3-dihydro-1H-inden-2-yl)glycine ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CC(C(=O)N(CC(=O)O)C1CC2=CC=CC=C2C1)NC(CCC3=CC=CC=C3)C(=O)O
• Isomeric SMILES: C[C@@H](C(=O)N(CC(=O)O)C1CC2=CC=CC=C2C1)N[C@@H](CCC3=CC=CC=C3)C(=O)O
• Uses: N-[(1S)-1-Carboxy-3-phenylpropyl]-L-alanyl-N-(2,3-dihydro-1H-inden-2-yl)glycine is an angiotensin-converting enzyme (ACE) inhibitor, similar to delapril.

Technology Process of Delapril diacid

There total 9 articles about Delapril diacid 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: 58.0%

delapril hydrochloride (83435-67-0) → Delaprilat (83398-08-7,83435-65-8)

Guidance literature:

With sodium hydroxide; In methanol;

DOI:10.1248/cpb.34.2852

Reference yield:

delapril (83435-67-0,110508-92-4,110508-93-5,83435-66-9) → ethanol (64-17-5) + Delaprilat (83398-08-7,83435-65-8)

Guidance literature:

With Tris-HCl buffer; human liver carboxylesterase pI 5.3; at 37 ℃; pH=7.4; Enzyme kinetics;

DOI:10.1248/bpb.20.869

Reference yield:

2-oxo-4-phenylbutanoic acid ethyl ester (64920-29-2) → Delaprilat (83398-08-7,83435-65-8)

Guidance literature:

Multi-step reaction with 6 steps

1: 29 percent / H₂, AcONa, AcOH, molecular sieves 3A / Raney Ni / ethanol

2: 93 percent / HCl / H₂O / 4 h

3: 68 percent / diethyl phosphorocyanidate, Et₃N / dimethylformamide / 1 h

4: 95 percent / HBr-AcOH 25percent / acetic acid / 0.17 h

5: 74 percent / NaHCO₃, 7N HCl / ethyl acetate; H₂O

6: 58 percent / 2N NaOH / methanol

With hydrogenchloride; sodium hydroxide; diethyl cyanophosphonate; 3 A molecular sieve; hydrogen bromide; hydrogen; sodium acetate; sodium hydrogencarbonate; acetic acid; triethylamine; nickel; In methanol; ethanol; water; acetic acid; ethyl acetate; N,N-dimethyl-formamide;

DOI:10.1248/cpb.34.2852

upstream raw materials:

delapril hydrochloride

delapril

2-oxo-4-phenylbutanoic acid ethyl ester

N--L-alanyl>-N-(indan-2-yl)glycine

Refernces

• 1、 Miyake,Itoh,Oka. "Design and synthesis of N-[N-[(S)-1-ethoxycarbonyl-3-phenylpropyl]-L-alanyl]-N-(indan-2-y l)glycine (CV-3317), a new, potent angiotensin converting enzyme inhibitor". . p. 2852 - 2858. Retrieved 2007/10/02.