(2S)-2-{[(tert-butoxy)carbonyl]amino}-3-phenylpropanoic acid

• ChemBase ID: 102310
• Molecular Formular: C14H19NO4
• Molecular Mass: 265.30496
• Monoisotopic Mass: 265.13140809
• SMILES: CC(C)(C)OC(=O)N[C@@H](Cc1ccccc1)C(=O)O
• Canonical SMILES: OC(=O)[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C14H19NO4/c1-14(2,3)19-13(18)15-11(12(16)17)9-10-7-5-4-6-8-10/h4-8,11H,9H2,1-3H3,(H,15,18)(H,16,17)/t11-/m0/s1
• InChIKey: ZYJPUMXJBDHSIF-NSHDSACASA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-{[(tert-butoxy)carbonyl]amino}-3-phenylpropanoic acid
• IUPAC Traditional name: (2S)-2-[(tert-butoxycarbonyl)amino]-3-phenylpropanoic acid
• Synonyms: N-(tert-Butoxycarbonyl)-L-phenylalanine; Boc-L-phenylalanine; Boc-Phe-OH; N-α-t-BOC-L-PHENYLALANINE; N-[(1,1-dimethylethoxy)carbonyl]-L-Phenylalanine; tert-Butoxycarbonyl-L-phenylalanine; (2S)-2-((tert-Butoxycarbonyl)amino)-3-phenylpropionic Acid; N-Boc-L-phenylalanine; N-(叔丁氧羰基)-L-苯基丙氨酸; Boc-L-苯丙氨酸

Database IDs

• CAS Number: 13734-34-4
• EC Number: 237-305-5
• MDL Number: MFCD00002663
• Beilstein Number: 2219729
• PubChem SID: 162088618; 24848166; 24849476
• PubChem CID: 77857

CALCULATED PROPERTIES

• Acid pKa: 4.0592823
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): 1.1170568
• LogD (pH = 7.4): -0.5543741
• Log P: 2.5697124
• Molar Refractivity: 69.9893 cm^3
• Polarizability: 27.498814 Å^3
• Polar Surface Area: 75.63 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Chloroform; Ethanol
• Apperance: White Solid
• Melting Point: 85-87 °C(lit.); 87-89°C
• Optical Rotation: [α]20/D +25±1°, c = 1% in ethanol

Safety Information

• Storage Condition: 0°C; Refrigerator
• German water hazard class: 3
• Personal Protective Equipment: Eyeshields, Gloves, type N95 (US), type P1 (EN143) respirator filter

Product Information

• Purity: ≥99%; ≥99.0% (T)
• Linear Formula: C6H5CH2CH(COOH)NHCOOC(CH3)3

DETAILS

MP Biomedicals - 02101090

Free Acid
Crystalline

Sigma Aldrich - 134562

Packaging
10 g in glass bottle

Sigma Aldrich - 15480

Packaging
5, 25, 100 g in glass bottle

Toronto Research Chemicals - B661530

Phenylalanine derivative used in enantioselective hydrolysis of amino acid esters. Acts as an inhibitor of gastric acid secretion.

REFERENCES

• Tomisaka, K. et al.: Chem. Comm., 1, 133 (2001)
• Magours, R., et al.: Biochim. Biophys. Acta, Mol. Cell Res., 858, 158 (1985)