(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(2-oxo-2,3-dihydro-1H-indol-3-yl)propanoic acid | CAS No. 1290040-14-0

(2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(2-oxo-2,3-dihydro-1H-indol-3-yl)propanoic acid

Basic Information

CAS Number

1290040-14-0

Molecular Formula

C26H22N2O5

Molecular Weight

442.46 g/mol

AD

Basic Physical Properties

O=C(N[C@H](C(=O)O)CC1C(=O)Nc2c1cccc2)OCC1c2ccccc2c2c1cccc2

InChI

InChI=1S/C26H22N2O5/c29-24-20(19-11-5-6-12-22(19)27-24)13-23(25(30)31)28-26(32)33-14-21-17-9-3-1-7-15(17)16-8-2-4-10-18(16)21/h1-12,20-21,23H,13-14H2,(H,27,29)(H,28,32)(H,30,31)/t20?,23-/m0/s1

InChIKey

JLKDRJNEVVDHFA-AKRCKQFNSA-N

LogP

4.104300000000003

Topological Polar Surface Area

104.73 Ų

Hydrogen Bond Donor/Acceptor

3 / 7

Complexity

735

Synonyms & References

English

  • (2S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-3-(2-oxoindolin-3-yl)propanoic acid
  • Fmoc-S-2,3-dihydro-2-oxo-Tryptophan
  • 2-(9H-Fluoren-9-ylmethoxycarbonylamino)-3-(2-oxo-1,3-dihydroindol-3-yl)propanoic acid
  • (2S)-2-({(9H-fluoren-9-yl)methoxycarbonyl}amino)-3-(2-oxo-2,3-dihydro-1H-indol-3-yl)propanoic acid

MDL Number

MFCD03844625

FAQ

What are the physical and chemical properties of (2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(2-oxo-2,3-dihydro-1H-indol-3-yl)propanoic acid (CAS: 1290040-14-0)?

The compound (2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(2-oxo-2,3-dihydro-1H-indol-3-yl)propanoic acid is a crystalline solid with a molecular weight of approximately 479.5 g/mol. Its solubility in water is low, and it is moderately soluble in organic solvents like DMSO. The compound is reactive towards nucleophilic attack, particularly at the amino and carboxylic acid functionalities. It is stable under normal temperature and pressure conditions but should be stored in a cool, dry place to maintain its structural integrity.

How is (2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(2-oxo-2,3-dihydro-1H-indol-3-yl)propanoic acid (CAS: 1290040-14-0) typically synthesized?

The compound is typically synthesized via a multi-step synthesis involving the formation of an amide through the coupling of a fluoren-9-yl methoxy carbonyl derivative with an indole-3-carboxylic acid. The use of appropriate catalysts such as HATU (O-(7-azabenzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate) and a base like DIPEA (N,N-diisopropylethylamine) is crucial for achieving high selectivity and yield. The final product is purified by recrystallization or HPLC.

What industries use (2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(2-oxo-2,3-dihydro-1H-indol-3-yl)propanoic acid (CAS: 1290040-14-0)?

This compound finds applications in the pharmaceutical industry, specifically in the development of novel pharmaceuticals with potential therapeutic effects. It is also used in the chemical industry, particularly in the synthesis of advanced organic materials and in the development of sensors and semiconductors. Its unique structural features make it a valuable intermediate in these fields.

What precautions should be taken when handling (2S)-2-({[(9H-fluoren-9-yl)methoxy]carbonyl}amino)-3-(2-oxo-2,3-dihydro-1H-indol-3-yl)propanoic acid (CAS: 1290040-14-0)?

When handling this compound, it is essential to wear appropriate personal protective equipment (PPE), including gloves, safety goggles, and lab coat. Ensure that the work is conducted in a fume hood to minimize inhalation risks. Spills should be cleaned up using appropriate absorbent materials, and the area should be well-ventilated. Always refer to the Material Safety Data Sheet (MSDS/SDS) for detailed information on storage, emergency procedures, and disposal methods.

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