(S)-2-benzyl-3-(tert-butoxycarbonylamino)propanoic acid

Basic Information

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CAS Number

189619-55-4

Molecular Formula

C15H21NO4

Molecular Weight

279.34 g/mol

Chemical Classification

Basic Chemical Raw Materials Organic Chemicals Carboxylic Acids

Basic Chemical Raw Materials Organic Chemicals Ethers

Fine Chemicals Dyes and Pigments Organic Dyes

Fine Chemicals Surfactants Anionic Surfactants

Basic Physical Properties

Melting Point

92-100 ºC

Boiling Point

441.3℃ at 760 mmHg

SMILES

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CC(C)(C)OC(=O)NCC(CC1=CC=CC=C1)C(=O)O

InChI

InChI=1S/C15H21NO4/c1-15(2,3)20-14(19)16-10-12(13(17)18)9-11-7-5-4-6-8-11/h4-8,12H,9-10H2,1-3H3,(H,16,19)(H,17,18)/t12-/m0/s1

InChIKey

ZYCITKXROAFBAR-LBPRGKRZSA-N

LogP

2.4546

Topological Polar Surface Area

75.63 Å²

Hydrogen Bond Donor/Acceptor

2 / 5

Complexity

329

Synonyms & References

English

(S)-2-Benzyl-3-((tert-butoxycarbonyl)amino)propanoic acid
(2R)-2-Benzyl-3-[(tert-butoxycarbonyl)-amino]propanoic acid
(2S)-2-Benzyl-3-((tert-butoxycarbonyl)-amino)propanoic acid
(S)-2-Benzyl-3-((tert-butoxycarbonyl)amino)propanoic
(S)-2-benzyl-3-(tert-butoxycarbonylamino)propanoic acid
Benzenepropanoic acid, a-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-,(aS)-
Benzenepropanoic acid, α-[[[(1,1-dimethylethoxy)carbonyl]amino]methyl]-, (αS)-
Boc-(S)-3-amino-2-benzylpropanoic acid
(2S)-2-Benzyl-3-[(tert-butoxycarbonyl)amino]propanoic acid
(2S)-3-Amino-2-benzylpropanoic acid, N-BOC protected
(S)-2-[(Boc-amino)methyl]-3-phenylpropionic acid
(Tert-Butoxy)Carbonyl (S)-3-Amino-2-benzylpropanoic acid
(2S)-2-(tert-Butoxycarbonylamino)methyl-3-phenylpropanoic acid
(2S)-2-{[(tert-Butoxycarbonyl)amino]methyl}-3-phenylpropanoic acid, (2S)-2-Benzyl-3-[(tert-butoxycarbonyl)amino]propanoic acid
(2S)-2-benzyl-3-{[(tert-butoxy)carbonyl]amino}propanoic acid
(2S)-2-benzyl-3-(tert-butoxycarbonylamino)propanoic acid
BENZENEPROPANOIC ACID, ALPHA-[[[(1,1-DIMETHYLETHOXY)CARBONYL]AMINO]METHYL]-, (ALPHAS)-
BOC-(S)-BETA2-HOMOPHENYLALANINE
189619-55-4
(S)-2-[(Boc-amino)methyl]-3-phenylpropionic acid, 97%
(2S)-N-Boc-3-amino-2-benzylpropionic acid
(S)-2-Benzyl-3-((tert-butoxycarbonyl)amino)propanoicacid
(2S)-2-BENZYL-3-[(TERT-BUTOXYCARBONYL)AMINO]PROPANOIC ACID
(S)-2-((tert-butoxycarbonyl)methyl)-3-phenylpropanoic acid;(S)-N-Boc-3-amino-2-benzylpropanoic Acid
(2S)-2-benzyl-3-[(2-methylpropan-2-yl)oxycarbonylamino]propanoic acid
A4187
F15186
DS-12800
DTXSID20426703
(2S)-2-Benzyl-3-[(tert-butoxycarbonyl)-amino]propanoic acid
(3S)-N-Boc-3-amino-2-benzylpropionic acid

MDL Number

MFCD07372495

FAQ

What are the physical and chemical properties of (S)-2-benzyl-3-(tert-butoxycarbonylamino)propanoic acid (CAS: 189619-55-4)?

(S)-2-Benzyl-3-(tert-butoxycarbonylamino)propanoic acid is a white crystalline solid with a molecular weight of approximately 331.43 g/mol. It has a pKa of around 4.5, indicating moderate acidity. The compound is poorly soluble in water but soluble in organic solvents like methanol and ethanol. Chemically, it is reactive towards nucleophiles, particularly amines, and can undergo esterification and amide formation under appropriate conditions.

How is (S)-2-benzyl-3-(tert-butoxycarbonylamino)propanoic acid (CAS: 189619-55-4) typically synthesized?

(S)-2-Benzyl-3-(tert-butoxycarbonylamino)propanoic acid can be synthesized by protecting the amino group of 2-benzylpropanoic acid with tert-butoxycarbonyl (Boc) using di-tert-butyldicarbonate (BDDC) in the presence of a base like triethylamine. The reaction typically occurs under mild conditions, and the product can be isolated by column chromatography or recrystallization.

What industries use (S)-2-benzyl-3-(tert-butoxycarbonylamino)propanoic acid (CAS: 189619-55-4)?

(S)-2-Benzyl-3-(tert-butoxycarbonylamino)propanoic acid finds applications in the pharmaceutical industry for the synthesis of peptide drugs. It is also used in the development of sensors and as a building block in polymer chemistry, particularly in the synthesis of biodegradable polymers. Its reactivity towards amines makes it valuable in organic synthesis and materials science.

What precautions should be taken when handling (S)-2-benzyl-3-(tert-butoxycarbonylamino)propanoic acid (CAS: 189619-55-4)?

When handling (S)-2-benzyl-3-(tert-butoxycarbonylamino)propanoic acid, it is essential to use appropriate personal protective equipment (PPE) such as gloves, goggles, and lab coats. Store the compound in a cool, dry place away from direct sunlight and heat sources. Use a fume hood during handling and synthesis to minimize exposure to volatiles. In case of spill, clean up with appropriate absorbents and dispose of according to local regulations. Refer to the Safety Data Sheet (SDS) for detailed information on handling and storage.