(2S)-2-[(3S)-3-{[(tert-butoxy)carbonyl]amino}-2-oxopyrrolidin-1-yl]-3-methylbutanoic acid

• ChemBase ID: 156158
• Molecular Formular: C14H24N2O5
• Molecular Mass: 300.35076
• Monoisotopic Mass: 300.16852188
• SMILES: CC(C)[C@@H](C(=O)O)N1CC[C@@H](C1=O)NC(=O)OC(C)(C)C
• Canonical SMILES: O=C(OC(C)(C)C)N[C@H]1CCN(C1=O)[C@H](C(=O)O)C(C)C
• InChI: InChI=1S/C14H24N2O5/c1-8(2)10(12(18)19)16-7-6-9(11(16)17)15-13(20)21-14(3,4)5/h8-10H,6-7H2,1-5H3,(H,15,20)(H,18,19)/t9-,10-/m0/s1
• InChIKey: KTNDZURPIXJJQU-UWVGGRQHSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-[(3S)-3-{[(tert-butoxy)carbonyl]amino}-2-oxopyrrolidin-1-yl]-3-methylbutanoic acid
• IUPAC Traditional name: (2S)-2-[(3S)-3-[(tert-butoxycarbonyl)amino]-2-oxopyrrolidin-1-yl]-3-methylbutanoic acid
• Synonyms: Boc-Gly-Val Freidinger’s lactam; N-Boc-Freidinger’s lactam; Boc-Gly-Val Freidinger 内酰胺; N-Boc-Freidinger 内酰胺

Database IDs

• CAS Number: 169950-87-2
• MDL Number: MFCD03100369
• PubChem SID: 162250296; 24850723
• PubChem CID: 17040185

CALCULATED PROPERTIES

• Acid pKa: 3.4922125
• H Acceptors: 4
• H Donor: 2
• LogD (pH = 5.5): -0.97949505
• LogD (pH = 7.4): -2.3580315
• Log P: 1.0196652
• Molar Refractivity: 74.7078 cm^3
• Polarizability: 29.528759 Å^3
• Polar Surface Area: 95.94 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Safety Information

• European Hazard Symbols: Irritant (Xi)
• German water hazard class: 3
• Risk Statements: 36/37/38
• Safety Statements: 26
• GHS Pictograms: GHS07
• GHS Signal Word: Warning
• GHS Hazard statements: H315-H319-H335
• GHS Precautionary statements: P261-P305 + P351 + P338
• Personal Protective Equipment: dust mask type N95 (US), Eyeshields, Gloves

Product Information

• Purity: ≥95.0% (HPLC)
• Grade: purum
• Empirical Formula (Hill Notation): C14H24N2O5

DETAILS

Sigma Aldrich - 17817

Application
Boc-protected conformationally restricted dipeptide peptidomimetic for Gly-Val-OH.
Other Notes
Boc-protected conformationally restricted dipeptide peptidomimetic for Gly-Val-OH1,2,3