(2R)-2-{[(tert-butoxy)carbonyl]amino}-2-cyclohexylacetic acid

• ChemBase ID: 38567
• Molecular Formular: C13H23NO4
• Molecular Mass: 257.32602
• Monoisotopic Mass: 257.16270822
• SMILES: C1C(CCCC1)[C@H](C(=O)O)NC(=O)OC(C)(C)C
• Canonical SMILES: O=C(OC(C)(C)C)N[C@H](C1CCCCC1)C(=O)O
• InChI: InChI=1S/C13H23NO4/c1-13(2,3)18-12(17)14-10(11(15)16)9-7-5-4-6-8-9/h9-10H,4-8H2,1-3H3,(H,14,17)(H,15,16)/t10-/m1/s1
• InChIKey: QSUXZIPXYDQFCX-SNVBAGLBSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2R)-2-{[(tert-butoxy)carbonyl]amino}-2-cyclohexylacetic acid
• IUPAC Traditional name: (R)-[(tert-butoxycarbonyl)amino](cyclohexyl)acetic acid
• Synonyms: (αR)-α-[[(1,1-Dimethylethoxy)carbonyl]amino]cyclohexaneacetic Acid; (2R)-2-[(tert-Butoxycarbonyl)amino]-2-(cyclohexyl)ethanoic Acid; (R)-2-(tert-Butoxycarbonylamino)-2-(cyclohexyl)acetic Acid; N-tert-Butoxycarbonyl-D-cyclohexylglycine; N-Boc-D-cyclohexylglycine; Boc-D-α-cyclohexylglycine; Boc-D-Chg-OH; Boc-D-Chg-OH; Boc-D-α-环己基甘氨酸

Database IDs

• CAS Number: 70491-05-3
• MDL Number: MFCD00133629
• Beilstein Number: 7689661
• PubChem SID: 161001874; 24849071
• PubChem CID: 7014890

CALCULATED PROPERTIES

• Acid pKa: 4.1653833
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.3193614
• LogD (pH = 7.4): -0.3858475
• Log P: 2.6708615
• Molar Refractivity: 66.3667 cm^3
• Polarizability: 26.41152 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 5
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Dichloromethane; DMSO; Ethyl Acetate
• Apperance: Off-White Solid

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥98.0% (TLC)
• Empirical Formula (Hill Notation): C13H23NO4

DETAILS

Sigma Aldrich - 15089

Packaging
1 g in poly tube
5 g in poly bottle

Toronto Research Chemicals - B646210

Intermediate in the preparation of Ximelagatran.

REFERENCES

• Thorstensson, F., et al.: Bioorg. Med. Chem., 15, 827 (2007)
• Nilsson, M., et al.: J. Med. Chem., 52, 2708 (2007)