ChemicalBook > CAS DataBase List > 5-1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene-2,2-dimethyl-1,3-dioxane-4,6-dione

5-1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene-2,2-dimethyl-1,3-dioxane-4,6-dione

Product Name
5-1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene-2,2-dimethyl-1,3-dioxane-4,6-dione
CAS No.
764667-64-3
Chemical Name
5-1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene-2,2-dimethyl-1,3-dioxane-4,6-dione
Synonyms
ethylidene);Sitagliptin-9;Sitagliptin Impurity 96;5-(1-Hydroxy-2-(2,4,5-trifluorophenyl);5-[1-Hydroxy-2-(2,4,5-trifluorophenyl)et;5-[1-hydroxy-2-92,4,5-trifluorophenyl0ethylidene]-2,2-dimethyl;5-[1-Hydroxy-2-(2,4,5-trifluorophenyl)ethylidene]-2,2-dimeth...;5-1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene-2,2-dimethyl-1,3-dioxane-4,6-dione;5-[1-Hydroxy-2-(2,4,5-trifluorophenyl)ethylidene]-2,2-diMethyl-1,3-dioxane-4,6-dion;1,3-Dioxane-4,6-dione,5-[1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene]-2,2-diMethyl-
CBNumber
CB31120915
Molecular Formula
C14H11F3O5
Formula Weight
316.23
MOL File
764667-64-3.mol
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5-1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene-2,2-dimethyl-1,3-dioxane-4,6-dione Property

Melting point:
117 °C (decomp)
Boiling point:
489.0±45.0 °C(Predicted)
Density 
1.462±0.06 g/cm3(Predicted)
storage temp. 
under inert gas (nitrogen or Argon) at 2-8°C
solubility 
Chloroform (Slightly), Ethyl Acetate (Slightly), Methanol (Slightly)
form 
Solid
pka
4.50±1.00(Predicted)
color 
White to Off-White
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Hazard and Precautionary Statements (GHS)

Symbol(GHS)
Signal word
Warning
Hazard statements

H302Harmful if swallowed

H315Causes skin irritation

H319Causes serious eye irritation

H335May cause respiratory irritation

Precautionary statements

P261Avoid breathing dust/fume/gas/mist/vapours/spray.

P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.

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N-Bromosuccinimide Price

TRC
Product number
H971700
Product name
5-[1-Hydroxy-2-(2,4,5-trifluorophenyl)ethylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
Packaging
1g
Price
$185
Updated
2021/12/16
Medical Isotopes, Inc.
Product number
59081
Product name
5-[1-Hydroxy-2-(2,4,5-trifluorophenyl)ethylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
Packaging
1g
Price
$650
Updated
2021/12/16
AK Scientific
Product number
Z1748
Product name
5-[1-Hydroxy-2-(2,4,5-trifluorophenyl)ethylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
Packaging
1g
Price
$71
Updated
2021/12/16
Chemenu
Product number
CM181663
Product name
5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
Purity
97%
Packaging
25g
Price
$153
Updated
2021/12/16
Crysdot
Product number
CD12035301
Product name
5-(1-Hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione
Purity
97%
Packaging
25g
Price
$166
Updated
2021/12/16
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5-1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene-2,2-dimethyl-1,3-dioxane-4,6-dione Chemical Properties,Usage,Production

Chemical Properties

White to Off-white Solid.

Uses

5-[1-Hydroxy-2-(2,4,5-trifluorophenyl)ethylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione is an impurity of the DPP-IV inhibitor Sitagliptin (S491000).

Application

5-[1-Hydroxy-2-(2,4,5-trifluorophenyl)ethylidene] is an intermediate for the synthesis of sitagliptin. Sitagliptin is a new type of anti-type II diabetes drug approved by the FDA and the first dipeptidyl peptidase-IV inhibitor drug for the treatment of type II diabetes.

Synthesis

2033-24-1

209995-38-0

764667-64-3

The general procedure for the synthesis of 5-[1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione from cyclo(isopropylidene)malonate (Meldrum acid) and 2,4,5-trifluorophenylacetic acid is as follows: in a 1000 mL three-necked flask, sequentially add 2,4,5-trifluorophenylacetic acid (25 g , 0.132 mol), Meldrum acid (21 g, 0.145 mol) and 4-dimethylaminopyridine (DMAP, 1.29 g, 0.0011 mol). Acetonitrile (75 mL) was added as a solvent in a single addition at room temperature. Subsequently, N,N-diisopropylethylamine (49.2 mL, 0.283 mol) was added as a one-time addition while keeping the reaction temperature below 40 °C. Next, pivaloyl chloride (17.8 mL, 0.145 mol) was slowly added dropwise over a period of 1 to 2 hours and the temperature was controlled to not exceed 40 °C. After the dropwise addition, the reaction mixture was stirred at 45-50 °C for 2-3 hours and then cooled to 0 °C. Over a period of 1 hour, 1N HCl (300 mL) was added slowly and dropwise to induce crystallization of the Meldrum acid adduct. The product was collected by filtration and washed with 20% aqueous acetonitrile. After drying, 36.5 g of Meldrum acid adduct was obtained in 88% yield. The structure of the product was confirmed by 1H-NMR (400 MHz, CDCl3) and 13C-NMR (100 MHz, CDCl3).

References

[1] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 9, p. 2622 - 2628
[2] Journal of the American Chemical Society, 2004, vol. 126, # 40, p. 13002 - 13009
[3] Journal of the American Chemical Society, 2009, vol. 131, # 25, p. 8798 - 8804
[4] Patent: WO2004/83212, 2004, A1. Location in patent: Page 11-12
[5] Patent: CN107501112, 2017, A. Location in patent: Paragraph 0061; 0062; 0063; 0064

5-1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene-2,2-dimethyl-1,3-dioxane-4,6-dione Preparation Products And Raw materials

Raw materials

Preparation Products

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5-1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene-2,2-dimethyl-1,3-dioxane-4,6-dione Suppliers

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View Lastest Price from 5-1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene-2,2-dimethyl-1,3-dioxane-4,6-dione manufacturers

Xinxiang Hongqi District Houyuan Trading Co.,Ltd
Product
5-1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene-2,2-dimethyl-1,3-dioxane-4,6-dione 764667-64-3
Price
US $30.00-28.00/Kg
Min. Order
1Kg
Purity
99.0% up
Supply Ability
50 tons per month
Release date
2023-05-31
Career Henan Chemical Co
Product
5-1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene-2,2-dimethyl-1,3-dioxane-4,6-dione 764667-64-3
Price
US $7.00/KG
Min. Order
1KG
Purity
99%
Supply Ability
JD 714
Release date
2019-09-01

764667-64-3, 5-1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene-2,2-dimethyl-1,3-dioxane-4,6-dioneRelated Search:

Sitagliptin Impurity 28 Sitagliptin Impurity 46 Sitagliptin Impurity 77 Sitagliptin impurity 5 Methyl 3-aMino-4-(2,4,5-trifluorophenyl)butanoate ethyl 3-oxo-4-(2,4,5-trifluorophenyl)butanoate 2-CHLOROMETHYL-5-TRIFLUOROMETHYL-[1,3,4]OXADIAZOLE Sitagliptin Impurity 34 2,4,5-TRIFLUOROBENZYL CHLORIDE (R)-methyl 3-acetamido-4-(2,4,5-trifluorophenyl)butanoate Benzenebutanoicacid,b-[[(1,1-diMethylethoxy)carbonyl]aMino]-2,4,5-trifluoro-,Methylester,(bR)- Sitagliptin Sitagliptin Impurity 14 Sitagliptin Defuoro IMpurity 5 Sitagliptin DeaMino IMpurity 1 (S)-Sitagliptin Phosphate 2,2,2-TRIFLUORO-N'-(TRIFLUOROACETYL)ACETOHYDRAZIDE (R)-10-(2,4,5-trifluorobenzyl)-3-(trifluoromethyl)-6,7,10,11-tetrahydro-[1,2,4]triazolo[3,4-c][1,4,7]triazecine-8,12(5H,9H)-dione

  • 5-1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene-2,2-dimethyl-1,3-dioxane-4,6-dione
  • 5-[1-Hydroxy-2-(2,4,5-trifluorophenyl)ethylidene]-2,2-diMethyl-1,3-dioxane-4,6-dion
  • 5-[1-hydroxy-2-92,4,5-trifluorophenyl0ethylidene]-2,2-dimethyl
  • 1,3-Dioxane-4,6-dione,5-[1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene]-2,2-diMethyl-
  • 5-[1-Hydroxy-2-(2,4,5-trifluorophenyl)-4,6-dionethylidene]-2,2-dimethyl-1,3-dioxane-4,6-dione
  • 5-(1-Hydroxy-2-(2,4,5-trifluorophenyl)
  • ethylidene)
  • Sitagliptin Impurity 96
  • Sitagliptin impurity 42/Sitagliptin Dioxo Impurity/5-(1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl- 1,3-dioxane-4,6-dione
  • Sitagliptin-9
  • 5-[1-Hydroxy-2-(2,4,5-trifluorophenyl)ethylidene]-2,2-dimeth...
  • 5-1-hydroxy-2-(2,4,5-trifluorophenyl)ethylidene-2,2-dimethyl-1,3-dioxane-4,6-dione 764667-64-3
  • 5-[1-Hydroxy-2-(2,4,5-trifluorophenyl)et
  • 5-(1-Hydroxy-2-(2,4,5-trifluorophenyl)ethylidene)-2,2-dimethyl-1,3-dioxane-4,6-dione (Sitagliptin Impurity)
  • 764667-64-3
  • Aromatics
  • Heterocycles
  • Impurities
  • Intermediates