(S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethanaMine
- Product Name
- (S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethanaMine
- CAS No.
- 608141-42-0
- Chemical Name
- (S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethanaMine
- Synonyms
- (S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethan-1-amine;Apremilast inter2;Apremilast Impurity 55;Apremilast Intermediate II;Apremilast Intermediates 2;Apremilast Impurity HS093220;Apremilast Desphthalyl Amine;RSSYY(Lurasidone Hydrochloride)-14;Apremilast EP Impurity H (S)-Isomer;(1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethanamine
- CBNumber
- CB82661858
- Molecular Formula
- C12H19NO4S
- Formula Weight
- 273.35
- MOL File
- 608141-42-0.mol
(S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethanaMine Property
- Melting point:
- 106-108oC
- Boiling point:
- 469.6±45.0 °C(Predicted)
- Density
- 1.195±0.06 g/cm3(Predicted)
- storage temp.
- Keep in dark place,Inert atmosphere,Room temperature
- solubility
- Chloroform (Slightly), Methanol (Slightly)
- pka
- 6.84±0.10(Predicted)
- form
- Solid
- color
- White to Off-White
- InChI
- InChI=1/C12H19NO4S/c1-4-17-12-7-9(5-6-11(12)16-2)10(13)8-18(3,14)15/h5-7,10H,4,8,13H2,1-3H3/t10-/s3
- InChIKey
- BXUJVINGXQGNFD-JQHDBZEONA-N
- SMILES
- [C@@H](C1C=CC(OC)=C(OCC)C=1)(N)CS(=O)(=O)C |&1:0,r|
Safety
- HS Code
- 2930909899
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.
N-Bromosuccinimide Price
- Product number
- M266045
- Product name
- (1S)-1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine
- Packaging
- 100mg
- Price
- $130
- Updated
- 2021/12/16
- Product number
- 2841AH
- Product name
- (1S)-1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine
- Packaging
- 1g
- Price
- $91
- Updated
- 2021/12/16
- Product number
- 2841AH
- Product name
- (1S)-1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine
- Packaging
- 5g
- Price
- $184
- Updated
- 2021/12/16
- Product number
- 2841AH
- Product name
- (1S)-1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine
- Packaging
- 10g
- Price
- $303
- Updated
- 2021/12/16
- Product number
- 2841AH
- Product name
- (1S)-1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine
- Packaging
- 25g
- Price
- $587
- Updated
- 2021/12/16
(S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethanaMine Chemical Properties,Usage,Production
Chemical Properties
APREMILAST intermediate is slightly soluble in dichloromethane and soluble in methanol. It is mainly used to synthesize APREMILAST. In addition, it can also regulate intracellular pro-inflammatory and anti-inflammatory factor effects through specificity for cyclic adenosine monophosphate (c AMP), which increases intracellular cAMP levels.
Uses
(1S)-1-(3-Ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine is an Apremilast (A729700) intermediate. Apremilast, an oral phosphodiesterase 4 inhibitor is used in the treatment of psoriatic arthritis.
Synthesis
1450657-31-4
608141-42-0
The general procedure for the synthesis of (S)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethylamine from the compound (CAS: 1450657-31-4) was as follows: bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate (36 mg, 0.074 mmol) and (S)-1-[(R)-2- ( diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine (40 mg, 0.074 mmol) were dissolved in 25 mL of 2,2,2-trifluoroethanol. Subsequently, 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethylamine (2.0 g, 7.4 mmol) was added to this solution. The reaction mixture was heated to 50 °C and hydrogenated under hydrogen pressure of 90 psig. After 18 h, the mixture was cooled to room temperature and removed from the hydrogenation unit. The solvent was removed by rotary evaporation and the residue was purified by chromatography on a C18 reversed-phase column using a water-acetonitrile gradient elution. The fraction containing the target product was collected and concentrated to about 150 mL. saturated brine (20 mL) was added to the concentrate and subsequently extracted with ethyl acetate (3 x 50 mL). The organic layers were combined, dried over anhydrous magnesium sulfate, filtered and concentrated to give a white crystalline solid product (1.4 g, 70% yield). The product was analyzed by non-chiral HPLC (Hypersil BDSC8, 5.0 μm, 250 × 4.6 mm, 1.5 mL/min, 278 nm, 90/10 to 80/20 0.1% TFA aqueous solution/methanol gradient elution for 10 min, followed by a gradient up to 10/90 0.1% TFA aqueous solution/methanol for the next 15 min). Retention time was 9.11 min (99.6% purity); chiral HPLC (Chiralpak AD-H 5.0 μm Daicel, 250 × 4.6 mm, 1.0 mL/min, 280 nm, 70:30:0.1 heptane-isopropanol-diethylamine) analyzed with retention times of 7.32 min (97.5%) and 8.26 min ( 2.47%).1H NMR (DMSO-d6) δ 1.32 (t, J = 7.0 Hz, 3H), 2.08 (s, 2H), 2.96 (s, 3H), 3.23 (dd, J = 3.6, 14.4 Hz, 1H), 3.41 (dd, J = 9.4, 14.4 Hz, 1H), 3.73 (s, 3H), 4.02 (q , J = 7.0 Hz, 2H), 4.26 (dd, J = 3.7, 9.3 Hz, 1H), 6.89 (s, 2H), 7.02 (s, 1H); 13C NMR (DMSO-d6) δ 14.77, 41.98, 50.89, 55.54, 62.03, 63.68, 111.48, 111.77, 118.36, 137.30, 147.93, 148.09.
References
[1] Patent: US2014/81032, 2014, A1. Location in patent: Paragraph 0318; 0319
[2] Patent: US2013/217919, 2013, A1. Location in patent: Paragraph 0280
[3] Patent: WO2016/199031, 2016, A1
(S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethanaMine Preparation Products And Raw materials
Raw materials
Preparation Products
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View Lastest Price from (S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethanaMine manufacturers
- Product
- (S)-1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine 608141-42-0
- Price
- US $0.00/kg
- Min. Order
- 1kg
- Purity
- 98%
- Supply Ability
- Customise
- Release date
- 2025-11-27
- Product
- (1S)-1-(3-ethoxy-4-methoxyphenyl)-2-methylsulfonylethanamine 608141-42-0
- Price
- US $2.00-6.00/kg
- Min. Order
- 1kg
- Purity
- 99%
- Supply Ability
- 100kg
- Release date
- 2025-08-08
- Product
- (S)-1-(3-Ethoxy-4-Methoxyphenyl)-2-(Methylsulfonyl)ethanaMine 608141-42-0
- Price
- US $10.00-7.00/kg
- Min. Order
- 1kg
- Purity
- 99.9%
- Supply Ability
- 20ton
- Release date
- 2024-06-06