N-[(2S)-3-amino-2-hydroxypropyl]-N-[3-fluoro-4-(morpholin-4-yl)phenyl]acetamide hydrochloride

• ChemBase ID: 160128
• Molecular Formular: C15H23ClFN3O3
• Molecular Mass: 347.8128232
• Monoisotopic Mass: 347.14119751
• SMILES: O1CCN(CC1)c1c(cc(cc1)N(C(=O)C)C[C@@H](O)CN)F.Cl
• Canonical SMILES: NC[C@@H](CN(c1ccc(c(c1)F)N1CCOCC1)C(=O)C)O.Cl
• InChI: InChI=1S/C15H22FN3O3.ClH/c1-11(20)19(10-13(21)9-17)12-2-3-15(14(16)8-12)18-4-6-22-7-5-18;/h2-3,8,13,21H,4-7,9-10,17H2,1H3;1H/t13-;/m0./s1
• InChIKey: NQKMMBPPUHHRKD-ZOWNYOTGSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: N-[(2S)-3-amino-2-hydroxypropyl]-N-[3-fluoro-4-(morpholin-4-yl)phenyl]acetamide hydrochloride
• IUPAC Traditional name: N-[(2S)-3-amino-2-hydroxypropyl]-N-[3-fluoro-4-(morpholin-4-yl)phenyl]acetamide hydrochloride
• Synonyms: (S)-N-(3-Amino-2-hydroxypropyl)-N-(3-fluoro-4-(4-morpholinylphenyl)acetamide HydrochlorideLinezolid Impurity; N-[(2S)-3-Amino-2-hydroxypropyl]-N-[3-fluoro-4-(4-morpholinyl)phenyl]acetamide Hydrochloride

Database IDs

• PubChem SID: 162254263
• PubChem CID: 71313241

CALCULATED PROPERTIES

• Acid pKa: 14.499777
• H Acceptors: 5
• H Donor: 2
• LogD (pH = 5.5): -3.2594743
• LogD (pH = 7.4): -2.0565815
• Log P: -0.32005116
• Molar Refractivity: 81.6687 cm^3
• Polarizability: 31.07451 Å^3
• Polar Surface Area: 79.03 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

DETAILS

Toronto Research Chemicals - A609075

N-[(2S)-3-Amino-2-hydroxypropyl]-N-[3-fluoro-4-(4-morpholinyl)phenyl]acetamide is one of the major thermal degradation products of Linezolid (L466500). Linezolid impurity.

REFERENCES

• Hadden, C.E., et al.: J. Heterocyclic Chem., 37, 1623 (2000)