1-tert-butyl 2-(2,5-dioxopyrrolidin-1-yl) (2S)-pyrrolidine-1,2-dicarboxylate

• ChemBase ID: 152408
• Molecular Formular: C14H20N2O6
• Molecular Mass: 312.3184
• Monoisotopic Mass: 312.13213637
• SMILES: CC(C)(C)OC(=O)N1CCC[C@H]1C(=O)ON1C(=O)CCC1=O
• Canonical SMILES: O=C([C@@H]1CCCN1C(=O)OC(C)(C)C)ON1C(=O)CCC1=O
• InChI: InChI=1S/C14H20N2O6/c1-14(2,3)21-13(20)15-8-4-5-9(15)12(19)22-16-10(17)6-7-11(16)18/h9H,4-8H2,1-3H3/t9-/m0/s1
• InChIKey: DICWIJISMKZDDY-VIFPVBQESA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: 1-tert-butyl 2-(2,5-dioxopyrrolidin-1-yl) (2S)-pyrrolidine-1,2-dicarboxylate
• IUPAC Traditional name: 1-tert-butyl 2-(2,5-dioxopyrrolidin-1-yl) (2S)-pyrrolidine-1,2-dicarboxylate
• Synonyms: Boc-L-proline N-hydroxysuccinimide ester; Boc-Pro-OSu; (2S)-1,2-Pyrrolidinedicarboxylic Acid 1-(1,1-Dimethylethyl) 2-(2,5-Dioxo-1-pyrrolidinyl) Ester; (2S)-2-[[(2,5-Dioxo-1-pyrrolidinyl)oxy]carbonyl]-1-pyrrolidinecarboxylic Acid 1,1-Dimethylethyl Ester; N-t-Boc-L-proline-N-hydroxysuccinimide Ester; Boc-Pro-OSu; Boc-L-脯氨酸 N-羟基琥珀酰亚胺酯

Database IDs

• CAS Number: 3392-10-7
• EC Number: 222-233-9
• MDL Number: MFCD00037902
• Beilstein Number: 497537
• PubChem SID: 24849312; 162246553
• PubChem CID: 853883

CALCULATED PROPERTIES

• Acid pKa: 17.704498
• H Acceptors: 4
• H Donor: 0
• LogD (pH = 5.5): 0.55563706
• LogD (pH = 7.4): 0.55563706
• Log P: 0.55563706
• Molar Refractivity: 73.6132 cm^3
• Polarizability: 29.208527 Å^3
• Polar Surface Area: 93.22 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: DMF; Ethanol; Methanol
• Apperance: White Cyrstalline Solid
• Melting Point: 123-125°C
• Optical Rotation: [α]20/D -56.0±1.0°, c = 2% in dioxane

Safety Information

• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter
• Storage Temperature: -20°C

Product Information

• Purity: ≥98.0% (N); 95+%
• Empirical Formula (Hill Notation): C14H20N2O6

DETAILS

Sigma Aldrich - 15491

Packaging
5 g in glass bottle

REFERENCES

• Rydzewski, R., et al.: Bioorg. Med. Chem., 10, 3277 (2002)
• Nilsson, M., et al.: J. Med. Chem., 52, 2708 (2002)