tert-butyl N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamate

• ChemBase ID: 69595
• Molecular Formular: C14H21NO3
• Molecular Mass: 251.32144
• Monoisotopic Mass: 251.15214354
• SMILES: C([C@@H](NC(=O)OC(C)(C)C)Cc1ccccc1)O
• Canonical SMILES: OC[C@H](Cc1ccccc1)NC(=O)OC(C)(C)C
• InChI: InChI=1S/C14H21NO3/c1-14(2,3)18-13(17)15-12(10-16)9-11-7-5-4-6-8-11/h4-8,12,16H,9-10H2,1-3H3,(H,15,17)/t12-/m0/s1
• InChIKey: LDKDMDVMMCXTMO-LBPRGKRZSA-N

NAMES AND DATABASE IDS

Names

• IUPAC name: tert-butyl N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamate
• IUPAC Traditional name: tert-butyl N-[(2S)-1-hydroxy-3-phenylpropan-2-yl]carbamate
• Synonyms: (S)-(-)-2-(tert-Butoxycarbonylamino)-3-phenyl-1-propanol; N-(tert-Butoxycarbonyl)-L-phenylalaninol; Boc-L-phenylalaninol; (S)-2-(Boc-amino)-3-phenyl-1-propanol; N-[(1S)-1-(Hydroxymethyl)-2-phenylethyl]carbamic Acid 1,1-Dimethylethyl Ester; (2S)-N-tert-Butoxycarbonyl-1-hydroxy-3-phenyl-2-propanamine; tert-Butyl [(1S)-1-Benzyl-2-hydroxyethyl]carbamate; N-Boc-L-phenylalaninol; Boc-L-phenylalaninol; (S)-(-)-2-(叔丁氧羰基氨基)-3-苯基-1-丙醇; N-(叔丁氧羰基)-L-苯丙氨醇; Boc-L-苯丙氨醇; (S)-2-(Boc-氨基)-3-苯基-1-丙醇

Database IDs

• CAS Number: 66605-57-0
• MDL Number: MFCD00076976
• Beilstein Number: 3652004
• PubChem SID: 162035321; 24849309; 24866394
• PubChem CID: 2733675

CALCULATED PROPERTIES

• Acid pKa: 14.370082
• H Acceptors: 2
• H Donor: 2
• LogD (pH = 5.5): 2.2494378
• LogD (pH = 7.4): 2.2494378
• Log P: 2.2494378
• Molar Refractivity: 70.1219 cm^3
• Polarizability: 27.580263 Å^3
• Polar Surface Area: 58.56 Å^2
• Rotatable Bonds: 6
• Lipinski's Rule of Five: true

PROPERTIES

Physical Property

• Solubility: Dichloromethane; Ethyl Acetate
• Apperance: Off-White Solid
• Melting Point: 94-96 °C(lit.); 95-98 °C
• Optical Rotation: [α]20/D -27±2°, c = 1% in methanol; [α]20/D -27°, c = 1 in chloroform

Safety Information

• Storage Warning: IRRITANT
• German water hazard class: 3
• TSCA Listed: false

Product Information

• Purity: ≥99.0% (sum of enantiomers, TLC); 95+%; 98%
• Grade: puriss.
• Optical Purity: ee: 99% (GLC)
• Linear Formula: C6H5CH2CH[NHCO2C(CH3)3]CH2OH

DETAILS

Sigma Aldrich - 421685

Application
Employed in the synthesis of biochemically active compounds. For references, see Aldrichimica Acta.1
Packaging
10 g in glass bottle

Toronto Research Chemicals - B661565

Protected L-Phenylalaninol, an intermediate in the preparation of (R)-Amphetamine.

REFERENCES

• Seefeld, M., et al.: Bioorg. Med. Chem. Lett., 19, 2244 (2009)
• Ji, H., et al.: J. Med. Chem., 52, 779 (2009)