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Ethyl N-carbobenzyloxy-L-phenylalaninate

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Identification
Molecular formula
C18H21NO4
CAS number
.None known
IUPAC name
ethyl (2S)-2-(benzyloxycarbonylamino)-3-phenyl-propanoate
State
State

At room temperature, Ethyl N-carbobenzyloxy-L-phenylalaninate is typically a solid. It will maintain this state in a stable environment free from excess moisture or high temperature.

Melting point (Celsius)
59.00
Melting point (Kelvin)
332.15
Boiling point (Celsius)
334.10
Boiling point (Kelvin)
607.30
General information
Molecular weight
313.35g/mol
Molar mass
313.3490g/mol
Density
1.1810g/cm3
Appearence

Ethyl N-carbobenzyloxy-L-phenylalaninate appears as a white to off-white crystalline powder. It can also sometimes be seen in a slightly yellow tint depending on purity and exposure to environmental conditions.

Comment on solubility

Solubility of Ethyl (2S)-2-(benzyloxycarbonylamino)-3-phenyl-propanoate

The solubility of ethyl (2S)-2-(benzyloxycarbonylamino)-3-phenyl-propanoate can be influenced by various factors due to its complex structure. Here’s a breakdown of its solubility characteristics:

  • Polar vs. Non-Polar Solvents: This compound is expected to exhibit solubility in organic solvents such as ethyl acetate and methanol, due to its polar functional groups. However, it is likely to be poorly soluble in highly polar solvents like water.
  • Hydrophobic Character: The presence of the phenyl group introduces some hydrophobic characteristics, which further indicates that solubility in non-polar solvents (like hexane) will be minimal.
  • Temperature Dependence: As with many organic compounds, solubility is often temperature-dependent. Increasing the temperature could enhance its solubility in certain organic solvents.
  • pH Sensitivity: The protonation state of the amino group may alter based on pH, potentially influencing solubility. Higher pH environments could increase solubility due to greater ionization.

In summary, the solubility behavior of ethyl (2S)-2-(benzyloxycarbonylamino)-3-phenyl-propanoate is complex and contingent upon solvent selection and environmental conditions. As the compound features both polar and non-polar elements, it exemplifies the principle that “like dissolves like,” and hence, careful consideration of the solvent is essential for its effective use in various applications.

Interesting facts

Interesting Facts about Ethyl (2S)-2-(benzyloxycarbonylamino)-3-phenyl-propanoate

Ethyl (2S)-2-(benzyloxycarbonylamino)-3-phenyl-propanoate is an intriguing compound with significant relevance in both organic chemistry and pharmaceuticals. Here are some captivating aspects of this compound:

  • Structure and Functionality: This compound features a complex structure, which includes both a benzyloxycarbonyl group and a phenyl group. This unique arrangement can influence its reactivity and how it interacts with other molecules.
  • Synthetic Utility: It acts as an important intermediate in the synthesis of various bioactive compounds, especially in the manufacture of amino acids and peptides. The benzyloxycarbonyl (Z) protective group is particularly valuable in peptide synthesis due to its stability and ease of removal.
  • Pharmaceutical Applications: Compounds related to this structure are often investigated for their pharmaceutical properties. They can have potential therapeutic roles in treating various diseases.
  • Chirality and Isomerism: Being a chiral molecule, it has optical isomers which can exhibit different biological activities or metabolic fates. Understanding its chiral nature is essential for medicinal chemistry.
  • Safety and Handling: Despite its usefulness, as with many chemical compounds, appropriate safety measures must be taken while handling and working with this ester due to potential reactivity and toxicity concerns.

This compound exemplifies the fascinating interplay between structure and function in organic chemistry. It encourages ongoing research, highlighting the importance of nuanced chemical design in developing new therapeutics.

Synonyms
28709-70-8
RefChem:1090732
N-((Phenylmethoxy)carbonyl)-L-phenylalanine ethyl ester
N-Carbobenzoxy-L-phenylalanine ethyl ester
ethyl (2S)-3-phenyl-2-(phenylmethoxycarbonylamino)propanoate
BRN 3004064
N-benzyloxycarbonyl-L-phenylalanine ethyl ester
L-N-Benzyloxycarbonyl-3-phenylalanine ethyl ester
SCHEMBL6440666
CHEMBL3275999
DTXSID30951354
XLLUIEKQXIOPDX-KRWDZBQOSA-N
ALANINE, N-BENZYLOXYCARBONYL-3-PHENYL-, ETHYL ESTER, L-
Ethyl N-[(benzyloxy)(hydroxy)methylidene]phenylalaninate