ethyl (2R,4R)-1-[(2S)-2-amino-5-(1-nitrocarbamimidamido)pentanoyl]-4-methylpiperidine-2-carboxylate hydrochloride

• ChemBase ID: 160200
• Molecular Formular: C15H29ClN6O5
• Molecular Mass: 408.88096
• Monoisotopic Mass: 408.18879574
• SMILES: N[C@@H](CCCNC(=N)N[N+](=O)[O-])C(=O)N1[C@H](C[C@@H](CC1)C)C(=O)OCC.Cl
• Canonical SMILES: CCOC(=O)[C@H]1C[C@H](C)CCN1C(=O)[C@H](CCCNC(=N)N[N+](=O)[O-])N.Cl
• InChI: InChI=1S/C15H28N6O5.ClH/c1-3-26-14(23)12-9-10(2)6-8-20(12)13(22)11(16)5-4-7-18-15(17)19-21(24)25;/h10-12H,3-9,16H2,1-2H3,(H3,17,18,19);1H/t10-,11+,12-;/m1./s1
• InChIKey: KYMBEZAOVMYAGM-QMCLHUHBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2R,4R)-1-[(2S)-2-amino-5-(1-nitrocarbamimidamido)pentanoyl]-4-methylpiperidine-2-carboxylate hydrochloride
• IUPAC Traditional name: ethyl (2R,4R)-1-[(2S)-2-amino-5-(1-nitrocarbamimidamido)pentanoyl]-4-methylpiperidine-2-carboxylate hydrochloride
• Synonyms: Argatroban Intermediate; (2R,4R)1-[(2S)2-Amino-5-[[imino(nitroamino)methyl]amino]-1-oxopentyl]-4-methyl-2-piperidinecarboxylic Acid Ethyl Ester Hydrochloride

Database IDs

• CAS Number: 74874-08-1
• PubChem SID: 162254335
• PubChem CID: 46780287

CALCULATED PROPERTIES

• Acid pKa: 10.029182
• H Acceptors: 8
• H Donor: 4
• LogD (pH = 5.5): -3.0615084
• LogD (pH = 7.4): -0.9166398
• Log P: -0.19241413
• Molar Refractivity: 104.5632 cm^3
• Polarizability: 36.1165 Å^3
• Polar Surface Area: 166.36 Å^2
• Rotatable Bonds: 9
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMSO; Methanol
• Apperance: Off White Solid
• Melting Point: 174-177°C

Safety Information

• Storage Condition: Hygroscopic, -20°C Freezer, Under inert atmosphere

DETAILS

Toronto Research Chemicals - A611695

Argatroban intermediate.

REFERENCES

• Abiko, Y., et al.: Thromb. Res., 24, 285 (1981)
• Kikumoto, R., et al.: Biochemistry, 23, 85 (1981)