ethyl (2R)-5-oxopyrrolidine-2-carboxylate

• ChemBase ID: 104577
• Molecular Formular: C7H11NO3
• Molecular Mass: 157.16714
• Monoisotopic Mass: 157.07389322
• SMILES: CCOC(=O)[C@H]1CCC(=O)N1
• Canonical SMILES: CCOC(=O)[C@H]1CCC(=O)N1
• InChI: InChI=1S/C7H11NO3/c1-2-11-7(10)5-3-4-6(9)8-5/h5H,2-4H2,1H3,(H,8,9)/t5-/m1/s1
• InChIKey: QYJOOVQLTTVTJY-RXMQYKEDSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: ethyl (2R)-5-oxopyrrolidine-2-carboxylate
• IUPAC Traditional name: ethyl (2R)-5-oxopyrrolidine-2-carboxylate
• Synonyms: D-Pyroglutamic acid ethyl ester; Ethyl 5-oxo-D-proline; Ethyl pyroglutamate; Ethyl (R)-(-)-2-pyrrolidone-5-carboxylate; (R)-5-Oxoproline ethyl ester; D-5-Oxo-2-pyrrolidinecarboxylic acid ethyl ester; 5-Oxo-D-proline Ethyl Ester; (R)-5-Oxopyrrolidine-2-carboxylic Acid Ethyl Ester; (R)-(-)-5-Ethylcarboxyl-2-pyrrolidinone; D-PYROGLUTAMIC ACID ETHYL ESTER; D-Pyroglutamic acid ethyl ester; (R)-Ethyl 5-oxopyrrolidine-2-carboxylate; 5-氧代-D-脯氨酸乙酯; D-焦谷氨酸乙酯; 焦谷氨酸乙酯; (R)-(-)-2-吡咯烷酮-5-羧酸乙酯; (R)-5-氧脯氨酸乙酯; D-5-氧代-2-吡咯烷羧酸乙酯; D-焦谷氨酸乙酯

Database IDs

• CAS Number: 68766-96-1
• MDL Number: MFCD00010848
• Beilstein Number: 82622
• PubChem SID: 24888089; 24858752; 162092220
• PubChem CID: 643508

CALCULATED PROPERTIES

• Acid pKa: 11.105785
• H Acceptors: 2
• H Donor: 1
• LogD (pH = 5.5): -0.38696864
• LogD (pH = 7.4): -0.38704345
• Log P: -0.3869677
• Molar Refractivity: 37.6055 cm^3
• Polarizability: 14.95568 Å^3
• Polar Surface Area: 55.4 Å^2
• Rotatable Bonds: 3
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Acetone; Chloroform; Ethanol; Methanol
• Apperance: Low Melting White Waxy Solid
• Melting Point: 49-53 °C(lit.); 53-57 °C
• Boiling Point: 168-171°C/1Hg; 176 °C/12 mmHg(lit.)
• Flash Point: >113 °C; >235.4 °F
• Refractive Index: n20/D 1.478(lit.)
• Optical Rotation: [α]/D -4.0±1°, c = 10 in ethanol; [α]20/D -4.0±1.0°, c = 10% in ethanol

Safety Information

• Storage Condition: Refrigerator
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99.0% (sum of enantiomers, HPLC); 95+%; 99%
• Grade: puriss.
• Optical Purity: enantiomeric ratio: ≥99:1 (GC)
• Empirical Formula (Hill Notation): C7H11NO3

DETAILS

MP Biomedicals - 02156462

(D-5-Oxo-2-pyrrolidinecarboxylic acid ethyl ester)

Sigma Aldrich - 309788

Packaging
1, 5 g in glass bottle

Sigma Aldrich - 83173

Other Notes
This ester of pyroglutamic acid can be transformed in many ways, e.g. N-alkylation1; Thionation of the lactam2; Preparation of the aldehyde3; Reduction to the hydroxymethyl compound4