[7-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-oxo-2H-chromen-4-yl]-aceticacid

Product Name: [7-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-oxo-2H-chromen-4-yl]-aceticacid
CAS No.: 378247-75-7
Chemical Name: [7-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-oxo-2H-chromen-4-yl]-aceticacid
Synonyms: Fmoc-7-aminocoumarin-4-acetic acid;Pyridine,2,3,6-trichloro-8-nitro-;N-Fmoc-Aminocoumarin-4-acetic acid;7-N-Fmoc-aminocoumarin-4-acetic acid;7-(Fmoc-amino)-2-oxo-2H-1-benzopyran-4-acetic acid;2-[7-(Fmoc-amino)-2-oxo-2H-chromen-4-yl]acetic Acid;7-(9-Fluorenylmethyloxycarbonylamino)-coumarin-4-acetic acid;[7-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-oxo-2H-chromen-4-yl]-aceticacid;7-[[(9H-Fluoren-9-ylmethoxy)carbonyl]amino]-2-oxo-2H-1-benzopyran-4-acetic acid;2-(7-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-oxo-2H-chromen-4-yl)aceticaci
CBNumber: CB82489625
Molecular Formula: C26H19NO6
Formula Weight: 441.43
MOL File: 378247-75-7.mol

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[7-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-oxo-2H-chromen-4-yl]-aceticacid Property

Melting point:: 273-276 °C
Boiling point:: 660.5±55.0 °C(Predicted)
Density: 1.418±0.06 g/cm3(Predicted)
storage temp.: Store at +2°C to +8°C.
pka: 4.23±0.10(Predicted)
form: powder
Appearance: White to off-white Solid

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Hazard and Precautionary Statements (GHS)

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N-Bromosuccinimide Price

Sigma-Aldrich

Product number: 8.52309
Product name: Fmoc-ACA-OH
Purity: Novabiochem<SUP>®</SUP>
Packaging: 250 mg
Price: $349
Updated: 2025/07/31

Sigma-Aldrich

Product number: 8.52309
Product name: Fmoc-ACA-OH
Purity: Novabiochem<SUP>®</SUP>
Packaging: 1 g
Price: $477
Updated: 2025/07/31

AK Scientific

Product number: KMA0040
Product name: 7-N-Fmoc-Aminocoumarin-4-aceticacid
Packaging: 100mg
Price: $264
Updated: 2021/12/16

Iris Biotech GmbH

Product number: RL-1170
Product name: Fmoc-ACA-OH
Packaging: 1g
Price: $270
Updated: 2021/12/16

AK Scientific

Product number: 2787CS
Product name: 2-(7-((((9H-Fluoren-9-yl)methoxy)carbonyl)amino)-2-oxo-2H-chromen-4-yl)aceticacid
Packaging: 100mg
Price: $293
Updated: 2021/12/16

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[7-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-oxo-2H-chromen-4-yl]-aceticacid Chemical Properties,Usage,Production

Uses

peptide synthesis

General Description

Fmoc-ACA-OH is a useful tool for the SPPS of AMC fluorogenic protease substrates. Fmoc-ACA-OH [1] must be first loaded onto a Wang-type resin. Any unreacted linker hydroxyls must be capped using acetic anhydride. Following Fmoc removal, the first amino acid should be coupled withy HATU/collidine [2]. Insertion of ACA into the middle of a peptide provides fluorogenic substrates for endopeptidases [3]. Treatment of the ACC peptide obtained after TFA cleavage with aqueous base causes facile decarboxylation and formation of the AMC peptide.

reaction suitability

reaction type: Fmoc solid-phase peptide synthesis

Synthesis

28920-43-6

85157-21-7

378247-75-7

The general procedure for the synthesis of (7-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-oxo-2H-chromen-4-yl)acetic acid from methyl chloroformate-9-fluorenyl and 7-amino-2-oxo-2H-1-chromen-4-acetic acid was as follows: 7-amino-2-oxo-2H-1-chromen-4-acetic acid (1.60 g, 5.6 mmol), NaOH (2.24 g, 56 mmol) and H2O (80 mL) were added to a 250 mL round bottom flask. The mixture was heated to reflux and kept overnight. Upon completion of the reaction, the reaction was quenched with water. Subsequently, the pH of the reaction mixture was adjusted to 2 with 4 M HCl and extracted three times with a solvent mixture of THF:EtOAc (5:1). The organic phases were combined and concentrated to afford the crude product 2-(7-amino-2-oxo-2H-chromen-4-yl)acetic acid (0.96 g, 4.38 mmol), which could be used directly in the next step of the reaction. 2-(7-Amino-2-oxo-2H-chromen-4-yl)acetic acid (1.00 g, 4.5 mmol) was dissolved in CH2Cl2 and TMSCl (1.45 g, 13.5 mmol) and DIPEA (1.74 g, 13.5 mmol) were added sequentially. The reaction mixture was heated to reflux for 3 hours. After completion of the reaction, the mixture was cooled in an ice bath. Fmoc-Cl (1.4 g, 5.4 mmol) was then added and stirred overnight at room temperature. At the end of the reaction, the reaction was quenched with 2M HCl (pH adjusted to 2) and extracted three times with a solvent mixture of THF:EtOAc (5:1). The organic phases were combined and concentrated, and the crude product was purified by column chromatography (THF:PE = 2:1 with 1.5% AcOH, Rf = 0.4) to afford the target compound Fmoc-ACC-OH (1.43 g, 3.24 mmol, 58% yield in two steps) as a white solid. The structure of the product was confirmed by 1H NMR, 13C NMR and HRMS.

References

[1] Journal of Organic Chemistry, 2002, vol. 67, # 3, p. 910 - 915
[2] Patent: US2002/22243, 2002, A1
[3] Patent: WO2005/110453, 2005, A2. Location in patent: Page/Page column 52
[4] Tetrahedron, 2016, vol. 72, # 27-28, p. 4085 - 4090

[7-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-oxo-2H-chromen-4-yl]-aceticacid Preparation Products And Raw materials

Raw materials

Preparation Products

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[7-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-oxo-2H-chromen-4-yl]-aceticacid Suppliers

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Sigma-Aldrich

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378247-75-7, [7-(9H-Fluoren-9-ylmethoxycarbonylamino)-2-oxo-2H-chromen-4-yl]-aceticacidRelated Search:

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378247-75-7