2-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]acetic acid

• ChemBase ID: 149563
• Molecular Formular: C11H11NO4
• Molecular Mass: 221.20934
• Monoisotopic Mass: 221.06880784
• SMILES: c1ccc(cc1)[C@H]1COC(=O)N1CC(=O)O
• Canonical SMILES: OC(=O)CN1C(=O)OC[C@@H]1c1ccccc1
• InChI: InChI=1S/C11H11NO4/c13-10(14)6-12-9(7-16-11(12)15)8-4-2-1-3-5-8/h1-5,9H,6-7H2,(H,13,14)/t9-/m1/s1
• InChIKey: PUKMRNJLFMISMT-SECBINFHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 2-[(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]acetic acid
• IUPAC Traditional name: [(4S)-2-oxo-4-phenyl-1,3-oxazolidin-3-yl]acetic acid
• Synonyms: (S)-(+)-2-Oxo-4-phenyl-3-oxazolidineacetic acid; (4s)-2-oxo-4-phenyl-3-oxazolidineacetic acid; (S)-(+)-2-氧代-4-苯基-3-噁唑烷乙酸

Database IDs

• CAS Number: 99333-54-7
• MDL Number: MFCD00192376
• PubChem SID: 24864372; 162243728
• PubChem CID: 853681

CALCULATED PROPERTIES

• Acid pKa: 3.7309802
• H Acceptors: 3
• H Donor: 1
• LogD (pH = 5.5): -0.64182144
• LogD (pH = 7.4): -2.1656718
• Log P: 1.1270535
• Molar Refractivity: 54.2813 cm^3
• Polarizability: 21.29183 Å^3
• Polar Surface Area: 66.84 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: 103-105 °C(lit.)
• Optical Rotation: [α]28/D +165°, c = 2 in chloroform

Safety Information

• German water hazard class: 3

Product Information

• Purity: 97%; 98%
• Empirical Formula (Hill Notation): C11H11NO4

DETAILS

Sigma Aldrich - 391344

Packaging
1 g in glass bottle
250 mg in glass bottle
Application
The chiral ketene derived from this product leads to chiral β-lactams via the Staudinger reaction.1 This strategy has been extended to prepare unnatural dipeptides.2