brivaracetam intermediate 2
Uses Application- Product Name
- brivaracetam intermediate 2
- CAS No.
- 78920-10-2
- Chemical Name
- brivaracetam intermediate 2
- Synonyms
- 5-hydroxy-4-propylfuran-2(5H)-one;4-n-Propyl hydroxy furanone;brivaracetam intermediate 2;5-Hydroxy-4-Propyl-2-Furanone;5-Hydroxy-4-n-propyl-2-furanone;5-hydroxy-4-n-propylfuran-2-one;2-hydroxy-3-propyl-2H-furan-5-one;5-Hydroxy-4-propyl-2(5H)-furanone;5-Hydroxy-4-propyl-5H-furan-2-one;5-hydroxy-4-propyl-1H-furan-2-one
- CBNumber
- CB52468656
- Molecular Formula
- C7H10O3
- Formula Weight
- 142.15
- MOL File
- 78920-10-2.mol
brivaracetam intermediate 2 Property
- Boiling point:
- 115 °C(Press: 0.01 Torr)
- Density
- 1.198±0.06 g/cm3(Predicted)
- vapor pressure
- 0.011-0.02Pa at 20-25℃
- storage temp.
- 2-8°C
- solubility
- Chloroform (Sparingly), Methanol (Slightly)
- pka
- 10.04±0.40(Predicted)
- form
- Oil
- color
- Yellow to Very Dark Brown
- InChI
- InChI=1S/C7H10O3/c1-2-3-5-4-6(8)10-7(5)9/h4,7,9H,2-3H2,1H3
- InChIKey
- KQMCGGGTJKNIMC-UHFFFAOYSA-N
- SMILES
- C(C1=CC(OC1O)=O)CC
- LogP
- 0.6 at 20℃ and pH6.4
- Surface tension
- 59.89mN/m at 1g/L and 20℃
Hazard and Precautionary Statements (GHS)
- Symbol(GHS)
-
- Signal word
- Warning
- Hazard statements
-
H314Causes severe skin burns and eye damage
H318Causes serious eye damage
- Precautionary statements
-
P260Do not breathe dust/fume/gas/mist/vapours/spray.
P264Wash hands thoroughly after handling.
P264Wash skin thouroughly after handling.
P280Wear protective gloves/protective clothing/eye protection/face protection.
P301+P330+P331IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P303+P361+P353IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304+P340IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P305+P351+P338IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continuerinsing.
P310Immediately call a POISON CENTER or doctor/physician.
P321Specific treatment (see … on this label).
P363Wash contaminated clothing before reuse.
P405Store locked up.
P501Dispose of contents/container to..…
N-Bromosuccinimide Price
- Product number
- A419310
- Product name
- 5-Hydroxy-4-propyl-5H-furan-2-one
- Packaging
- 100mg
- Price
- $60
- Updated
- 2021/12/16
- Product number
- CHM0390770
- Product name
- 5-HYDROXY-4-PROPYLFURAN-2(5H)-ONE
- Purity
- 95.00%
- Packaging
- 5MG
- Price
- $505.4
- Updated
- 2021/12/16
- Product number
- CS-B0865
- Product name
- 5-Hydroxy-4-propyl-5H-furan-2-one
- Purity
- 99.59%
- Packaging
- 25g
- Price
- $53
- Updated
- 2021/12/16
- Product number
- J56806
- Product name
- 5-Hydroxy-4-propylfuran-2(5H)-one
- Packaging
- 25g
- Price
- $110
- Updated
- 2021/12/16
- Product number
- A128277
- Product name
- 5-Hydroxy-4-propylfuran-2(5H)-one
- Purity
- 98%
- Packaging
- 100g
- Price
- $181
- Updated
- 2021/12/16
brivaracetam intermediate 2 Chemical Properties,Usage,Production
Uses
4-Propyl-5-hydroxyfuran-2-one can be used as a pharmaceutical synthesis intermediate, such as in the preparation of brivaracetam. Brivaracetam, chemically named (2S)-2-[(4R)-2-oxo-4-n-propylpyrrolidine]butanamide, is a novel antiepileptic drug developed by UCB in Belgium.
Application
4-Propyl-5-hydroxyfuran-2-one can be used as a pharmaceutical synthesis intermediate, as shown in the following reaction:
First, an appropriate amount of 18g of (S)-2-aminobutyramide hydrochloride is released in 100mL of ammonia in isopropanol solution (3.3-3.7mol/L), and then reacted with 19g of 4-propyl-5-hydroxyfuran-2-one at room temperature; 18.44g of solid product is obtained. Yield 61.0%. Alternatively, a solution of isopropanol containing 5-hydroxy-4-n-propyl-furan-2-one was slowly added dropwise to a solution of free (S)-2-aminobutyramide in isopropanol, and the mixture was magnetically stirred overnight at room temperature. The reaction was then carried out directly to the next step without further treatment. ESI-MS (m/z): 227 [M+H]+.
Synthesis
110-62-3
298-12-4
78920-10-2
General procedure for the synthesis of 5-hydroxy-4-propyl-2(5H)-furanone from n-pentanal and 2-oxoacetic acid (example of an industrial batch): the amounts of all materials were calculated based on the amount of glyoxalic acid in 50% w/w glyoxalate solution. (0050) Heptane (1285 kg, 1889 L, 4.04 v/v) and morpholine (595 L, 601.3 kg, 6902 mol, 1.09 equiv) were added to the reactor. After the addition of morpholine, the dosing equipment was flushed with heptane (20 L, 0.04 v/v). The mixed solution was stirred at 22-23 °C for 10 min and subsequently cooled to 4.4 °C. (0051) A 50% aqueous solution of glyoxalate (935 kg, 6318 mol, 1.0 eq.) was slowly added, controlling the rate of addition to keep the reaction temperature below 40 °C. Upon completion of addition, the addition equipment was flushed with heptane (20 L, 0.04 v/v). The reaction mixture was stirred at a temperature range of 30.9 to 23.8 °C for 2 hours. Subsequently, n-pentanal (706 L, 576.8 kg, 6697 mol, 1.06 eq.) was slowly added, again controlling the rate of addition to keep the temperature below 40 °C. (0052) Upon completion of n-pentanal addition, the addition equipment was flushed with heptane (40 L, 0.08 v/v). The material in the reactor was heated to 40.1-41.7 °C and the reaction was maintained at this temperature for 18 hours and 04 minutes. Upon completion of the reaction, the mixture was cooled to 22.8 °C and aqueous hydrochloric acid (1168 L, 1.73 eq.) was slowly added at this temperature, controlling the rate of addition to maintain the temperature between 23.5-25.0 °C. The reaction was then purged by stirring. After completion of acid addition, the reaction mixture was continued to be stirred for 4 hours. (0053) The reaction mixture was allowed to stand to separate the organic phase after layering. The aqueous phase was washed three times with heptane (3 x 943 L, 3 x 2 v/v). Diisopropyl ether (1322 kg, 1888 L, 4.04 v/v) was added to the aqueous phase, followed by the addition of solid sodium carbonate (199 kg) in batches until the pH reached 0.4. After standing and stratifying the mixture, the organic phase was separated. The target compound (II) was extracted from the aqueous phase with diisopropyl ether (2 × 530 kg, 2 × 756 L, 2 × 1.6 v/v). All organic phases were combined and washed once with 20% w/w aqueous sodium chloride solution (944.2 kg, 1.6 v/v). Subsequently, the organic layer was dried by azeotropic distillation under vacuum (jacket temperature not exceeding 40 °C) and filtered. Finally, the solution was concentrated under vacuum below 40 °C and filtered by polishing through a 10 μm cartridge filter. Correction for water content (3.7%) and DIPE content (3.8%) based on the total mass of water (934.9 kg) resulted in 864.8 kg of compound (II) (6084 mol, 96.3% yield).
References
[1] Patent: WO2017/76738, 2017, A1. Location in patent: Page/Page column 6-7
[2] Patent: CN106748950, 2017, A. Location in patent: Paragraph 0064; 0065; 0081; 0082; 0098; 0099; 0115; 0116
[3] Synthetic Communications, 2018, vol. 48, # 1, p. 85 - 90
[4] Patent: WO2011/86565, 2011, A1. Location in patent: Page/Page column 23-24
[5] Patent: WO2011/86566, 2011, A1. Location in patent: Page/Page column 24
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View Lastest Price from brivaracetam intermediate 2 manufacturers
- Product
- 2(5H)-FURANONE, 5-HYDROXY-4-PROPYL- 78920-10-2
- Price
- US $100.00/KG
- Min. Order
- 100G
- Purity
- 98%
- Supply Ability
- 500KG
- Release date
- 2018-07-25