(2S)-2-amino-3,3-dimethylbutanoic acid

• ChemBase ID: 70001
• Molecular Formular: C6H13NO2
• Molecular Mass: 131.17292
• Monoisotopic Mass: 131.09462866
• SMILES: C(=O)([C@@H](N)C(C)(C)C)O
• Canonical SMILES: N[C@@H](C(C)(C)C)C(=O)O
• InChI: InChI=1S/C6H13NO2/c1-6(2,3)4(7)5(8)9/h4H,7H2,1-3H3,(H,8,9)/t4-/m1/s1
• InChIKey: NPDBDJFLKKQMCM-SCSAIBSYSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: (2S)-2-amino-3,3-dimethylbutanoic acid
• IUPAC Traditional name: (2S)-2-amino-3,3-dimethylbutanoic acid
• Synonyms: L-2-tert-Butylglycine; (S)-2-Amino-3,3-dimethylbutyric acid; L-α-tert-Butylglycine; L-tert-Leucine; L-tert-Leucine; (S)-2-氨基-3,3-二甲基丁酸; L-α-叔丁基甘氨酸; L-叔亮氨酸

Database IDs

• CAS Number: 20859-02-3
• EC Number: 424-750-7
• MDL Number: MFCD00064218
• Beilstein Number: 1721824
• PubChem SID: 24856311; 162035726
• PubChem CID: 164608

CALCULATED PROPERTIES

• Acid pKa: 2.7936387
• H Acceptors: 3
• H Donor: 2
• LogD (pH = 5.5): -1.5744301
• LogD (pH = 7.4): -1.5785921
• Log P: -1.5740803
• Molar Refractivity: 33.891 cm^3
• Polarizability: 13.835553 Å^3
• Polar Surface Area: 63.32 Å^2
• Rotatable Bonds: 2
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Melting Point: >300°C; ≥300 °C(lit.)
• Optical Rotation: [α]20/D +7±1°, c = 5% in 5 M HCl; [α]20/D -9.5°, c = 3 in H2O; +7 (c=5 in 5N HCl)

Safety Information

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

Product Information

• Purity: ≥99.0% (NT); 95+%; 99%
• Grade: puriss.
• Optical Purity: ee: 99% (GLC)
• Impurities: ~0.5% water
• Linear Formula: (CH3)3CCH(NH2)CO2H

DETAILS

Sigma Aldrich - 269107

Packaging
1, 5, 25 g in glass bottle

REFERENCES

• ɑ-Amino acids have been used in combination with NaBH₄ for the asymmetric reduction of ketones. Of a number of amino acids the sterically hindered tert-leucine was found to give the highest ee (95%) in the reduction of the carbonyl group of a 1,5-benzothiazepine intermediate in an efficient synthesis of the calcium antagonist diltiazem: J. Org. Chem., 61, 8586 (1996).