Amiglumide

Base Information

• Chemical Name: Amiglumide
• CAS No.: 119363-62-1
• Molecular Formula: C₂₆H₃₆N₂O₄
• Molecular Weight: 440.583
• UNII: H48W1A97VB
• Nikkaji Number: J442.661D
• Wikidata: Q27279626
• NCI Thesaurus Code: C74181
• ChEMBL ID: CHEMBL114325
• Mol file: 119363-62-1.mol

Synonyms:Amiglumide;Amiglumide [INN];119363-62-1;UNII-H48W1A97VB;CHEMBL114325;H48W1A97VB;(R)-4-(2-Naphthamido)-N,N-dipentylglutaramic acid;4-Dipentylcarbamoyl-4-[(naphthalene-2-carbonyl)-amino]-butyric acid;SCHEMBL1056352;BDBM50008667;CR1795;Q27279626;(4R)-5-(dipentylamino)-4-(naphthalene-2-carbonylamino)-5-oxopentanoic acid

Chemical Property of Amiglumide

Chemical Property:

• Vapor Pressure: 7.15E-20mmHg at 25°C
• Boiling Point: 687.9°Cat760mmHg
• Flash Point: 369.9°C
• PSA: 90.20000
• Density: 1.117g/cm³
• LogP: 5.58680
• XLogP3: 5.5
• Hydrogen Bond Donor Count: 2
• Hydrogen Bond Acceptor Count: 4
• Rotatable Bond Count: 14
• Exact Mass: 440.26750763
• Heavy Atom Count: 32
• Complexity: 584

Purity/Quality:

99% ^*data from raw suppliers

AMIGLUMIDE 95.00% ^*data from reagent suppliers

Safty Information:

• Pictogram(s):  
• Hazard Codes: 

MSDS Files:

SDS file from LookChem

Useful:

• Canonical SMILES: CCCCCN(CCCCC)C(=O)C(CCC(=O)O)NC(=O)C1=CC2=CC=CC=C2C=C1
• Isomeric SMILES: CCCCCN(CCCCC)C(=O)[C@@H](CCC(=O)O)NC(=O)C1=CC2=CC=CC=C2C=C1

Technology Process of Amiglumide

There total 4 articles about Amiglumide 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:

(2R)-5-(benzyloxy)-2-{[(benzyloxy)carbonyl]amino}-5-oxopentanoic acid (59486-73-6) → Amiglumide (119363-62-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) triethylamine, ethyl chloroformate / 1.) THF, -10 deg C, 15 min, 2.)a) THF, -10 deg C, 1 h, b) RT, 3 h

2: H₂, H₂O / 10percent Pd/activated charcoal / methanol / 2 h / 760 Torr / Ambient temperature

3: aq. NaOH / tetrahydrofuran / 3 h / Ambient temperature

With sodium hydroxide; water; hydrogen; chloroformic acid ethyl ester; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1021/jm00079a003

Reference yield:

(R)-4-Benzyloxycarbonylamino-4-dipentylcarbamoyl-butyric acid benzyl ester (119777-40-1) → Amiglumide (119363-62-1)

Guidance literature:

Multi-step reaction with 2 steps

1: H₂, H₂O / 10percent Pd/activated charcoal / methanol / 2 h / 760 Torr / Ambient temperature

2: aq. NaOH / tetrahydrofuran / 3 h / Ambient temperature

With sodium hydroxide; water; hydrogen; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1021/jm00079a003

Reference yield:

Di-n-amylamine (2050-92-2) → Amiglumide (119363-62-1)

Guidance literature:

Multi-step reaction with 3 steps

1: 1.) triethylamine, ethyl chloroformate / 1.) THF, -10 deg C, 15 min, 2.)a) THF, -10 deg C, 1 h, b) RT, 3 h

2: H₂, H₂O / 10percent Pd/activated charcoal / methanol / 2 h / 760 Torr / Ambient temperature

3: aq. NaOH / tetrahydrofuran / 3 h / Ambient temperature

With sodium hydroxide; water; hydrogen; chloroformic acid ethyl ester; triethylamine; palladium on activated charcoal; In tetrahydrofuran; methanol;

DOI:10.1021/jm00079a003

upstream raw materials:

(R)-4-Amino-4-dipentylcarbamoyl-butyric acid

2-naphthaloyl chloride

(2R)-5-(benzyloxy)-2-{[(benzyloxy)carbonyl]amino}-5-oxopentanoic acid

(R)-4-Benzyloxycarbonylamino-4-dipentylcarbamoyl-butyric acid benzyl ester