[ CAS No. 608142-27-4 ] {[proInfo.proName]}

Name: 608142-27-4|(R)-1-(3-Ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine|97%
Brand: Ambeed
SKU: A895748
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Product Details of [ 608142-27-4 ]

CAS No. :	608142-27-4	MDL No. :	MFCD22643957
Formula :	C₁₂H₁₉NO₄S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	BXUJVINGXQGNFD-JTQLQIEISA-N
M.W :	273.35	Pubchem ID :	10195080
Synonyms :

Safety of [ 608142-27-4 ]

Signal Word:	Warning	Class:
Precautionary Statements:	P264-P280-P302+P352-P337+P313-P305+P351+P338-P362+P364-P332+P313	UN#:
Hazard Statements:	H315-H319	Packing Group:
GHS Pictogram:

Application In Synthesis of [ 608142-27-4 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Upstream synthesis route of [ 608142-27-4 ]
Downstream synthetic route of [ 608142-27-4 ]

[ 608142-27-4 ] Synthesis Path-Upstream 1~6

1
[ 1450657-31-4 ]
[ 608141-42-0 ]
[ 608142-27-4 ]

Yield	Reaction Conditions	Operation in experiment
94.4 % ee	With bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; (2R)-1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-[bis[4-(trifluoromethyl)phenyl]phosphino]ferrocene; hydrogen In 2,2,2-trifluoroethanol at 50℃; for 18 h; Inert atmosphere	General procedure: For each reaction, a mixture of bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate (9 mg, 0.018 mmol), 2,2,2-trifluoroethanol (3 mL), and the appropriate ligand (0.037 mmol) or a preformed complex of the ligand and metal (0.018 mmol) was prepared under nitrogen. Then, 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethenamine (100 mg, 0.37 mmol) was added. The resultant mixture was heated to 50° C. and hydrogenated under 250 psig hydrogen pressure. After 18 h, the mixture was removed from the hydrogenator and monitored by achiral HPLC (Hypersil BDS C₈, 5.0 μm, 250×4.6 mm, 1.5 mL/min, 278 nm, 90/10 gradient to 80/20 0.1percent aqueous TFA/MeOH over 10 min then gradient to 10/90 0.1percent aqueous TFA/MeOH over the next 15 min). Reactions containing >10 Area percent of the product enamine were also assayed for chiral purity by chiral HPLC (Chiralpak AD-H 5.0 μm Daicel, 250×4.6 mm, 1.0 mL/min, 280 nm, 70:30:0.1 heptane-1-PrOH-diethylamine or 50:40:10:0.1 heptane-EtOH-i-PrOH-diethylamine). The results are listed in Table 1 below.
85.99 % ee	With Ru(OAc)2((R)-dm-segphos); hydrogen In 2,2,2-trifluoroethanol at 50℃; for 18 h; Inert atmosphere	General procedure: For each reaction, a mixture of bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate (9 mg, 0.018 mmol), 2,2,2-trifluoroethanol (3 mL), and the appropriate ligand (0.037 mmol) or a preformed complex of the ligand and metal (0.018 mmol) was prepared under nitrogen. Then, 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethenamine (100 mg, 0.37 mmol) was added. The resultant mixture was heated to 50° C. and hydrogenated under 250 psig hydrogen pressure. After 18 h, the mixture was removed from the hydrogenator and monitored by achiral HPLC (Hypersil BDS C₈, 5.0 μm, 250×4.6 mm, 1.5 mL/min, 278 nm, 90/10 gradient to 80/20 0.1percent aqueous TFA/MeOH over 10 min then gradient to 10/90 0.1percent aqueous TFA/MeOH over the next 15 min). Reactions containing >10 Area percent of the product enamine were also assayed for chiral purity by chiral HPLC (Chiralpak AD-H 5.0 μm Daicel, 250×4.6 mm, 1.0 mL/min, 280 nm, 70:30:0.1 heptane-1-PrOH-diethylamine or 50:40:10:0.1 heptane-EtOH-i-PrOH-diethylamine). The results are listed in Table 1 below.
25.72 % ee	Stage #1: With sodium tetrahydroborate; (S)-valinol In tetrahydrofuran at -10 - 0℃; for 1 h; Stage #2: With boron trifluoride diethyl etherate In tetrahydrofuran at -10 - 30℃;	To a 2 L round bottom flask equipped with a mechanical stirrer, thermometer, and condenser, charge 500 mL of THF followed by (£/Z)- l-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl) ethenamine (50 grams, 0.184 mole) at 25-30 °C. The mixture was cooled at -10 °C to 0 °C. Charge sodium borohydride (8.36 grams, 0.221 mole) and L-valinol (4.7 grams, 0.046 mole) to reaction mass and stir for 1 hour at -10 °C to 0 °C. To the cooled the reaction mass add mixture of Borontrifluoride diethyl etherate (28.56 mL, 0.221 moles) in THF (30 mL) in 1 hour at - 10 to 0 °C. The mixture was allowed to warm at 25-30 °C in 2-3 hours and stirred overnight at 25-30 °C. Water (250 mL) was charged to reaction mass at 0-10 °C. After warming to 25-30 °C, the THF was distilled out from reaction mixture under vacuum. Charge ethyl acetate (200 mL) to reaction mass and add concentrated Hydrochloric acid (50 mL) till pH 2-3. Separate the organic and aqueous layer. To the aqueous layer charge 30 percent sodium hydroxide (225 mL) till pH 10-1 1. Extract the compound by using dichloromethane (2 *250 mL). Club the organic layers and wash with 10 percent aqueous sodium chloride solution. Distilled off dichloromethane for organic layer. To the crude solid charge THF (25 mL) and stir for 30 minutes. Filter the isolated solid on Buchner funnel. The wet solid dried in hot air oven at 40-45 °C for 4 hours to provide l-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine as off white solid (41.7 grams, 83 percent yield). NMR (DMSO-d⁶) δ 1.35 (t, 3H), 2.09 (bs, 2H), 2.96 (s, 3H), 3.2 (m, 1H), 3.4 (m, 1H), 3.73 (s, 3H), 4.05 (q, 2H), 4.28 (m,l H), 6.89 (s, 2H), 7.02 (s, lH)^~ppm;FTIR (KBr): 907, 1025, 1 142, 1256, 1312, 1517, 1590, 2983, 3362 cm-';MS (ESI) m/z= 274.23 (M+l );Chiral HPLC: 37.14percent (R-Isomer): 62.86percent (S-isomer).

Reference： [1] Patent: US2013/217919, 2013, A1, . Location in patent: Paragraph 0280
[2] Patent: US2013/217919, 2013, A1, . Location in patent: Paragraph 0280
[3] Patent: WO2017/179065, 2017, A1, . Location in patent: Page/Page column 15

2
[ 60758-86-3 ]
[ 608141-42-0 ]
[ 608142-27-4 ]

Reference： [1] Patent: US2013/217919, 2013, A1,
[2] Patent: WO2017/179065, 2017, A1,

3
[ 253168-94-4 ]
[ 608141-42-0 ]
[ 608142-27-4 ]

Reference： [1] Patent: WO2016/161996, 2016, A1,
[2] Patent: WO2016/161996, 2016, A1,

4
[ 608142-27-4 ]
[ 608141-42-0 ]

Reference： [1] Patent: WO2016/199031, 2016, A1,

5
[ 60758-79-4 ]
[ 608141-42-0 ]
[ 608142-27-4 ]

Reference： [1] Patent: WO2017/179065, 2017, A1,

6
[ 121-32-4 ]
[ 608141-42-0 ]
[ 608142-27-4 ]

Reference： [1] Patent: WO2017/179065, 2017, A1,

[ 608142-27-4 ] Synthesis Path-Downstream 1~26

1
[ 6296-53-3 ]
[ 608142-27-4 ]
[ 608141-44-2 ]

Reference： [1]ChemCatChem,2019,vol. 11,p. 5808 - 5813
[2]Journal of Medicinal Chemistry,2009,vol. 52,p. 1522 - 1524

2
[ 253168-94-4 ]
[ 608142-27-4 ]

Reference： [1]Journal of Medicinal Chemistry,2009,vol. 52,p. 1522 - 1524
[2]Patent: EP2431371,2012,A1

3
[ 621-59-0 ]
[ 608142-27-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1.1: potassium carbonate / N,N-dimethyl-formamide / 20 °C / Inert atmosphere 2.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere 2.2: 20 °C / Cooling with salt-ice; Inert atmosphere 3.1: hydrogenchloride; water / diethyl ether / 0.5 h / 20 °C 3.2: pH 12 / Cooling with ice 4.1: methanol / 8 h / 20 °C / Reflux; Inert atmosphere 5.1: sodium hydroxide / dichloromethane; water / pH 11 / Cooling with ice

Reference： [1]Current Patent Assignee: GANZHOU HEMAY PHARMACEUTICAL - EP2431371, 2012, A1

4
[ 1131-52-8 ]
[ 608142-27-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1.1: n-butyllithium / tetrahydrofuran; hexane / -78 °C / Inert atmosphere 1.2: 20 °C / Cooling with salt-ice; Inert atmosphere 2.1: hydrogenchloride; water / diethyl ether / 0.5 h / 20 °C 2.2: pH 12 / Cooling with ice 3.1: methanol / 8 h / 20 °C / Reflux; Inert atmosphere 4.1: sodium hydroxide / dichloromethane; water / pH 11 / Cooling with ice

Reference： [1]Current Patent Assignee: GANZHOU HEMAY PHARMACEUTICAL - EP2431371, 2012, A1

5
[ 1255909-21-7 ]
[ 608142-27-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: hydrogenchloride; water / diethyl ether / 0.5 h / 20 °C 1.2: pH 12 / Cooling with ice 2.1: methanol / 8 h / 20 °C / Reflux; Inert atmosphere 3.1: sodium hydroxide / dichloromethane; water / pH 11 / Cooling with ice

Reference： [1]Current Patent Assignee: GANZHOU HEMAY PHARMACEUTICAL - EP2431371, 2012, A1

6
[ 608142-28-5 ]
[ 608142-27-4 ]

Yield	Reaction Conditions	Operation in experiment
	With sodium hydroxide In dichloromethane; water Cooling with ice;	(R)-1-(3-ethoxy-4-methoxvphenyl)-2-(methylsulfonyl)ethylamine Compound 4d; (R)-1-(3-ethoxy-4-methoxvphenyl)-2-(methylsulfonyl)ethylamine To a 250 ml of single-neck flask equipped with a magnetic stirrer were added compound 4c, 50 ml of dichloromethane and 50 ml of water. To the mixture was added dropwise 5% sodium hydroxide aqueous solution in an ice bath to adjust pH to 11. The resultant mixture was separated. The aqueous layer was extracted with 50 ml of dichloromethane. The dichloromethane layers were combined. The organic phase was washed with 50 ml of saturated NaCl, dried over anhydrous MgSO4, and filtered. The solvent was evaporated to give 0.622 g of a white solid (99.0% ee). MS (m/z): 274 [M+1]+; Chiral HPLC (isopropyl alcohol/n-hexane/diethylamine = 35/65/0.1, chiralcel OJ-H column, 250 * 4.6 mm, 1.0 mL/min, 234 nm): 15.2 min (R-isomer, 99.5%), 17.3 min (S-isomer,0.5%).

Reference： [1]Current Patent Assignee: GANZHOU HEMAY PHARMACEUTICAL - EP2431371, 2012, A1 Location in patent: Page/Page column 25

7
[ 60758-86-3 ]
[ 608142-27-4 ]

Reference： [1]Patent: US2013/217919,2013,A1

8
N-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-2-methylpropane-2(R)-sulfinamide [ No CAS ]
[ 608141-42-0 ]
[ 608142-27-4 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; In methanol; diethyl ether; at 20 - 25℃; for 12h;	Finally, a reaction flask was charged with Compound 27 F in 29 MeOH (10 vol) at 20-25 C. then treated with 2N 25 HCl/30 Et2O (2 mL, 2.0 equiv) and stirred for 12 h. The reaction mixture was concentrated to dryness and the resulting solid was dissolved in 31 water/32 EtOAc. The aqueous portion was neutralized then extracted with CH2Cl2. The combined organic layers were dried with MgSO4 then concentrated to provide 10 (S)-1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonylethylamine (Compound B).

Reference： [1]Patent: US2013/217918,2013,A1 .Location in patent: Paragraph 0167

9
[ 1450657-31-4 ]
[ 608141-42-0 ]
[ 608142-27-4 ]

Yield	Reaction Conditions	Operation in experiment
	With bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; (2R)-1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-[bis[4-(trifluoromethyl)phenyl]phosphino]ferrocene; hydrogen; In 2,2,2-trifluoroethanol; at 50℃; under 13689.1 Torr; for 18h;Inert atmosphere;	General procedure: For each reaction, a mixture of bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate (9 mg, 0.018 mmol), 2,2,2-trifluoroethanol (3 mL), and the appropriate ligand (0.037 mmol) or a preformed complex of the ligand and metal (0.018 mmol) was prepared under nitrogen. Then, 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethenamine (100 mg, 0.37 mmol) was added. The resultant mixture was heated to 50 C. and hydrogenated under 250 psig hydrogen pressure. After 18 h, the mixture was removed from the hydrogenator and monitored by achiral HPLC (Hypersil BDS C8, 5.0 mum, 250×4.6 mm, 1.5 mL/min, 278 nm, 90/10 gradient to 80/20 0.1% aqueous TFA/MeOH over 10 min then gradient to 10/90 0.1% aqueous TFA/MeOH over the next 15 min). Reactions containing >10 Area % of the product enamine were also assayed for chiral purity by chiral HPLC (Chiralpak AD-H 5.0 mum Daicel, 250×4.6 mm, 1.0 mL/min, 280 nm, 70:30:0.1 heptane-1-PrOH-diethylamine or 50:40:10:0.1 heptane-EtOH-i-PrOH-diethylamine). The results are listed in Table 1 below.
	With Ru(OAc)2((R)-dm-segphos); hydrogen; In 2,2,2-trifluoroethanol; at 50℃; under 13689.1 Torr; for 18h;Inert atmosphere;	General procedure: For each reaction, a mixture of bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate (9 mg, 0.018 mmol), 2,2,2-trifluoroethanol (3 mL), and the appropriate ligand (0.037 mmol) or a preformed complex of the ligand and metal (0.018 mmol) was prepared under nitrogen. Then, 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethenamine (100 mg, 0.37 mmol) was added. The resultant mixture was heated to 50 C. and hydrogenated under 250 psig hydrogen pressure. After 18 h, the mixture was removed from the hydrogenator and monitored by achiral HPLC (Hypersil BDS C8, 5.0 mum, 250×4.6 mm, 1.5 mL/min, 278 nm, 90/10 gradient to 80/20 0.1% aqueous TFA/MeOH over 10 min then gradient to 10/90 0.1% aqueous TFA/MeOH over the next 15 min). Reactions containing >10 Area % of the product enamine were also assayed for chiral purity by chiral HPLC (Chiralpak AD-H 5.0 mum Daicel, 250×4.6 mm, 1.0 mL/min, 280 nm, 70:30:0.1 heptane-1-PrOH-diethylamine or 50:40:10:0.1 heptane-EtOH-i-PrOH-diethylamine). The results are listed in Table 1 below.
		To a 2 L round bottom flask equipped with a mechanical stirrer, thermometer, and condenser, charge 500 mL of THF followed by (£/Z)- l-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl) ethenamine (50 grams, 0.184 mole) at 25-30 C. The mixture was cooled at -10 C to 0 C. Charge sodium borohydride (8.36 grams, 0.221 mole) and L-valinol (4.7 grams, 0.046 mole) to reaction mass and stir for 1 hour at -10 C to 0 C. To the cooled the reaction mass add mixture of Borontrifluoride diethyl etherate (28.56 mL, 0.221 moles) in THF (30 mL) in 1 hour at - 10 to 0 C. The mixture was allowed to warm at 25-30 C in 2-3 hours and stirred overnight at 25-30 C. Water (250 mL) was charged to reaction mass at 0-10 C. After warming to 25-30 C, the THF was distilled out from reaction mixture under vacuum. Charge ethyl acetate (200 mL) to reaction mass and add concentrated Hydrochloric acid (50 mL) till pH 2-3. Separate the organic and aqueous layer. To the aqueous layer charge 30 % sodium hydroxide (225 mL) till pH 10-1 1. Extract the compound by using dichloromethane (2 *250 mL). Club the organic layers and wash with 10 % aqueous sodium chloride solution. Distilled off dichloromethane for organic layer. To the crude solid charge THF (25 mL) and stir for 30 minutes. Filter the isolated solid on Buchner funnel. The wet solid dried in hot air oven at 40-45 C for 4 hours to provide l-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine as off white solid (41.7 grams, 83 % yield). NMR (DMSO-d6) delta 1.35 (t, 3H), 2.09 (bs, 2H), 2.96 (s, 3H), 3.2 (m, 1H), 3.4 (m, 1H), 3.73 (s, 3H), 4.05 (q, 2H), 4.28 (m,l H), 6.89 (s, 2H), 7.02 (s, lH)~ppm;FTIR (KBr): 907, 1025, 1 142, 1256, 1312, 1517, 1590, 2983, 3362 cm-';MS (ESI) m/z= 274.23 (M+l );Chiral HPLC: 37.14% (R-Isomer): 62.86% (S-isomer).

Reference： [1]Patent: US2013/217919,2013,A1 .Location in patent: Paragraph 0280
[2]Patent: US2013/217919,2013,A1 .Location in patent: Paragraph 0280
[3]Patent: WO2017/179065,2017,A1 .Location in patent: Page/Page column 15

10
[ 1450657-31-4 ]
[ 608142-27-4 ]

Yield	Reaction Conditions	Operation in experiment
70%	With bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate; (2R)-1-[(1R)-1-[bis(1,1-dimethylethyl)phosphino]ethyl]-2-(diphenylphosphino)ferrocene; hydrogen In 2,2,2-trifluoroethanol at 50℃; for 18h; Inert atmosphere;	2 EXAMPLE 2 Synthesis of (R)-1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethanamine A solution of bis(1,5-cyclooctadiene)rhodium(I) trifluoromethanesulfonate (36 mg, 0.074 mmol) and (R)-1-[(S)-2-(diphenylphosphino)ferrocenyl]ethyldi-tert-butylphosphine (40 mg, 0.074 mmol) in 25 mL of 2,2,2-trifluoroethanol was prepared under nitrogen. To this solution was then charged 1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethenamine (2.0 g, 7.4 mmol). The resulting mixture was heated to 50° C. and hydrogenated under 90 psig hydrogen pressure. After 18 h, the mixture was cooled to ambient temperature and removed from the hydrogenator. The mixture was evaporated and the residue was purified by chromatography on a C18 reverse phase column using a water-acetonitrile gradient. The appropriate fractions were pooled and evaporated to 150 mL. To this solution was added brine (20 mL), and the resulting solution was extracted with EtOAc (3×50 mL). The combined organic layers were dried (MgSO4) and evaporated to provide the product as a white crystalline solid (1.4 g, 70% yield); achiral HPLC (Hypersil BDS C8, 5.0 μm, 250×4.6 mm, 1.5 mL/min, 278 nm, 90/10 gradient to 80/20 0.1% aqueous TFA/MeOH over 10 min then gradient to 10/90 0.1% aqueous TFA/MeOH over the next 15 min): 9.11 (99.6%); chiral HPLC (Chiralpak AD-H 5.0 μm Daicel, 250×4.6 mm, 1.0 mL/min, 280 nm, 70:30:0.1 heptane-i-PrOH-diethylamine): 7.32 (97.5%), 8.26 (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.

Reference： [1]Current Patent Assignee: AMGEN INC - US2013/217919, 2013, A1 Location in patent: Paragraph 0276-0277

11
[ 60758-86-3 ]
[ 608141-42-0 ]
[ 608142-27-4 ]

Reference： [1]Patent: US2013/217919,2013,A1
[2]Patent: WO2017/179065,2017,A1

12
C₁₂H₁₉NO₄S*C₁₀H₁₀ClNO₅ [ No CAS ]
[ 608141-42-0 ]
[ 608142-27-4 ]

Yield	Reaction Conditions	Operation in experiment
1.01 g	With sodium hydroxide; In water;	Pure salt of formula (S)-4aa is obtained from 3.0 g (10.98 mmol) of the racemic amine of formula 2a through the method described in Example 4. The amount of 0.93 g of NaOM (23.3 mmol) is added to the aqueous mother liquors and the released amine (mixture of (R)-2a> (S)-2a) is extracted with dichioromethane (3x 20 ml). The organic phase is dried with anhydrous Na2SO4 and subsequently evaporated on an evaporator at a reduced pressure. Thisprovides 1.50 g of a mixture of (R)-2a> (S)-2a (ee 54%). The white solid substance obtained this way is dissolved in 12 ml of methanol in a hot state, inoculated with the racemic amine of formula 2a and stirred overnight at the room temperature. After aspiration of the produced crystals and washing with methanol (2x 1 ml) the amount of 0.48 g (yield 70%) of the racemic amine of formula 2a (ee 0%) is obtained. Evaporation of the mother liquors can provide thecompound of formula (R)-2a (1.01 g; ee 79%)

Reference： [1]Patent: WO2016/161996,2016,A1 .Location in patent: Page/Page column 22

13
[ 253168-94-4 ]
[ 608141-42-0 ]
[ 608142-27-4 ]

Reference： [1]ChemCatChem,2019,vol. 11,p. 5808 - 5813
[2]Patent: WO2016/161996,2016,A1
[3]Patent: WO2016/161996,2016,A1

14
[ 608142-27-4 ]
[ 1450657-31-4 ]

Yield	Reaction Conditions	Operation in experiment
1.40 g	With N-acetylleucine; sode de l'acide trichloroisocyanurique; sodium hydroxide In dichloromethane; water at 25℃; for 0.75h;	10 Example 10: Preparation of 1 -(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethen- 1-amine (IV) (R)- 1 -(3-ethoxy-4-methoxy-phenyl)-2-methanesulfonyl-ethylamine of formula (Vb) containing 20% N-Ac-Leucine (1.56 g, 5.06 mmol, 82.9% ee) was dissolved in dichloromethane (60 mL) at room temperature. Water (15 mL) was added and the pH of the solution was adjusted to 9.5 with 1M sodium hydroxide. NaDCC (712 mg, 2.76 mmol) was added to the reaction mixture and the pH decreased to 8.9. The mixture was vigorously stirred for 45 minutes at 25°C. Water (30 mL) was added to the reaction mixture and layers were separated. DBU (825 jiL, 5.52 mmol) was added to the organic layer and stirred for 1 h at room temperature. The reaction mixture was washed with water (10 mL) and brine (10 mL), dried over magnesium sulfate and evaporated to dryness to provide the title compound as a yellow solid.Yield: 1.40 g (>99%).

Reference： [1]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - WO2016/199031, 2016, A1 Location in patent: Page/Page column 31; 32

15
[ 608142-27-4 ]
[ 608141-42-0 ]

Reference： [1]Patent: WO2016/199031,2016,A1

16
[ 608142-27-4 ]
[ 608141-41-9 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: sodium hydroxide; sode de l'acide trichloroisocyanurique; N-acetylleucine / water; dichloromethane / 0.75 h / 25 °C / pH 8.9-9.5 2: sodium cyanoborohydride; citric acid / methanol / 1 h / 5 °C 3: acetic acid / water / 3 h / 20 - 97 °C 4: N,N-dimethyl-formamide / 8 h / 20 - 95 °C
	Multi-step reaction with 5 steps 1: sodium hydroxide; sode de l'acide trichloroisocyanurique; N-acetylleucine / water; dichloromethane / 0.75 h / 25 °C / pH 8.9-9.5 2: sodium cyanoborohydride; citric acid / methanol / 1 h / 5 °C 3: acetic acid / water / 3 h / 20 - 97 °C 4: sodium hydroxide / water; toluene / 3 h / 20 °C 5: acetic acid / toluene / 100 - 105 °C
	Multi-step reaction with 3 steps 1: acetic acid / 80 - 85 °C / Large scale 2: palladium 10% on activated carbon; hydrogen / ethanol / 25 - 30 °C / Large scale 3: 135 - 139 °C / Large scale

Reference： [1]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - WO2016/199031, 2016, A1
[2]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - WO2016/199031, 2016, A1
[3]Current Patent Assignee: WUHAN HITECK BIOLOGICAL PHARMA CO LTD - CN106748962, 2017, A

17
[ 608142-27-4 ]
1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonylethylamine (2R,3R)-2,3-bis((4-methylbenzoyl)oxy)succinic acid salt [ No CAS ]
1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonylethylamine (2R,3R)-2,3-bis((4-methylbenzoyl)oxy)succinic acid salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium hydroxide; sode de l'acide trichloroisocyanurique; N-acetylleucine / water; dichloromethane / 0.75 h / 25 °C / pH 8.9-9.5 2: sodium cyanoborohydride; citric acid / methanol / 1 h / 5 °C 3: acetic acid / methanol; N,N-dimethyl-formamide / 2 h / 20 - 65 °C

Reference： [1]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - WO2016/199031, 2016, A1

18
[ 608142-27-4 ]
1-(3-ethoxy-4-methoxyphenyl)-2-methanesulfonylethylamine (-)-dibenzoyl-L-tartaric acid salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium hydroxide; sode de l'acide trichloroisocyanurique; N-acetylleucine / water; dichloromethane / 0.75 h / 25 °C / pH 8.9-9.5 2: sodium cyanoborohydride; citric acid / methanol / 1 h / 5 °C 3: acetic acid / water / 3 h / 20 - 97 °C

Reference： [1]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - WO2016/199031, 2016, A1

19
[ 608142-27-4 ]
C₄₅H₄₈N₄O₁₄S₂ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: sodium hydroxide; sode de l'acide trichloroisocyanurique; N-acetylleucine / water; dichloromethane / 0.75 h / 25 °C / pH 8.9-9.5 2: sodium cyanoborohydride; citric acid / methanol / 1 h / 5 °C 3: 3 h / 98 - 100 °C

Reference： [1]Current Patent Assignee: DR REDDY'S LABORATORIES LIMITED - WO2016/199031, 2016, A1

20
[ 60758-79-4 ]
[ 608141-42-0 ]
[ 608142-27-4 ]

Reference： [1]Patent: WO2017/179065,2017,A1

21
[ 121-32-4 ]
[ 608141-42-0 ]
[ 608142-27-4 ]

Reference： [1]Patent: WO2017/179065,2017,A1

22
[ 641-70-3 ]
[ 608142-27-4 ]
C₂₀H₂₀N₂O₈S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84.2%	With acetic acid at 80 - 85℃; Large scale;	Preparation of intermediate 1 To a 50 L reactor was added acetic acid 6.0 L, starting material 1 3.00 Kg,Starting material 2 4.03Kg, stirring heated to 80 ~ 85 ° C, the reaction 3 ~ 5h,TLC method for the detection of the reaction end, when the disappearance of SMII as the reaction was complete.The reaction is completed, cooled to 60 ~ 65 ,Dropping anhydrous ethanol / purified water (1/4) 36.0L, stirring to precipitate an oily solid,Heated to 60 ~ 65 ° C until the oil-like solid dissolved, cooling crystallization,Stirred at room temperature for 1 ~ 2h, filtered, the filter cake was washed with purified water 1.5L,45 ~ 50 blast drying 6 ~ 8h, pale yellow solid.The light yellow solid was added to a 50L autoclave, isopropanol was added 15.0L,Stirring and heating to 60 ~ 65 stirring 30min, cooled to room temperature, filtered,Filter cake was dried at 40 ~ 45 4 ~ 6h, intermediate I 5.85Kg.Yield 84.2%.

Reference： [1]Current Patent Assignee: WUHAN HITECK BIOLOGICAL PHARMA CO LTD - CN106748962, 2017, A Location in patent: Paragraph 0022

23
[ 608142-27-4 ]
[ 635705-72-5 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: acetic acid / 80 - 85 °C / Large scale 2: palladium 10% on activated carbon; hydrogen / ethanol / 25 - 30 °C / Large scale

Reference： [1]Current Patent Assignee: WUHAN HITECK BIOLOGICAL PHARMA CO LTD - CN106748962, 2017, A

24
(E)-2-ethoxy-1-methoxy-4-(2-(methylsulfonyl)vinyl)benzene [ No CAS ]
[ 608142-27-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: hydroxylamine hydrochloride; triethylamine / ethanol / 24 h / 80 °C 2: zinc; acetic acid 3: N-Ac-Leu / methanol

Reference： [1]Jana, Anupam; Zieliński, Grzegorz Krzysztof; Czarnocka-Śniadała, Sylwia; Grudzień, Krzysztof; Podwysocka, Dominika; Szulc, Marcin; Kajetanowicz, Anna; Grela, Karol [ChemCatChem, 2019, vol. 11, # 23, p. 5808 - 5813]

25
C₁₂H₁₉NO₅S [ No CAS ]
[ 608142-27-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: zinc; acetic acid 2: N-Ac-Leu / methanol

26
2-ethoxy-1-methoxy-4-vinylbenzene [ No CAS ]
[ 608142-27-4 ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: 1,3-bis-(2,4,6-trimethylphenyl)-2-(imidazolidinylidene)dichloro(5-nitro-2-isopropoxyphenylmethylene)ruthenium / 0.83 h / 120 °C / Microwave irradiation 2: hydroxylamine hydrochloride; triethylamine / ethanol / 24 h / 80 °C 3: zinc; acetic acid 4: N-Ac-Leu / methanol

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[ 608142-27-4 ]

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Ghs Precautionary Statements

Precautionary Statements-General
Code	Phrase
P101	If medical advice is needed,have product container or label at hand.
P102	Keep out of reach of children.
P103	Read label before use
Prevention
Code	Phrase
P201	Obtain special instructions before use.
P202	Do not handle until all safety precautions have been read and understood.
P210	Keep away from heat/sparks/open flames/hot surfaces. - No smoking.
P211	Do not spray on an open flame or other ignition source.
P220	Keep/Store away from clothing/combustible materials.
P221	Take any precaution to avoid mixing with combustibles
P222	Do not allow contact with air.
P223	Keep away from any possible contact with water, because of violent reaction and possible flash fire.
P230	Keep wetted
P231	Handle under inert gas.
P232	Protect from moisture.
P233	Keep container tightly closed.
P234	Keep only in original container.
P235	Keep cool
P240	Ground/bond container and receiving equipment.
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P261	Avoid breathing dust/fume/gas/mist/vapours/spray.
P262	Do not get in eyes, on skin, or on clothing.
P263	Avoid contact during pregnancy/while nursing.
P264	Wash hands thoroughly after handling.
P265	Wash skin thouroughly after handling.
P270	Do not eat, drink or smoke when using this product.
P271	Use only outdoors or in a well-ventilated area.
P272	Contaminated work clothing should not be allowed out of the workplace.
P273	Avoid release to the environment.
P280	Wear protective gloves/protective clothing/eye protection/face protection.
P281	Use personal protective equipment as required.
P282	Wear cold insulating gloves/face shield/eye protection.
P283	Wear fire/flame resistant/retardant clothing.
P284	Wear respiratory protection.
P285	In case of inadequate ventilation wear respiratory protection.
P231 + P232	Handle under inert gas. Protect from moisture.
P235 + P410	Keep cool. Protect from sunlight.
Response
Code	Phrase
P301	IF SWALLOWED:
P304	IF INHALED:
P305	IF IN EYES:
P306	IF ON CLOTHING:
P307	IF exposed:
P308	IF exposed or concerned:
P309	IF exposed or if you feel unwell:
P310	Immediately call a POISON CENTER or doctor/physician.
P311	Call a POISON CENTER or doctor/physician.
P312	Call a POISON CENTER or doctor/physician if you feel unwell.
P313	Get medical advice/attention.
P314	Get medical advice/attention if you feel unwell.
P315	Get immediate medical advice/attention.
P320
P302 + P352	IF ON SKIN: wash with plenty of soap and water.
P321
P322
P330	Rinse mouth.
P331	Do NOT induce vomiting.
P332	IF SKIN irritation occurs:
P333	If skin irritation or rash occurs:
P334	Immerse in cool water/wrap n wet bandages.
P335	Brush off loose particles from skin.
P336	Thaw frosted parts with lukewarm water. Do not rub affected area.
P337	If eye irritation persists:
P338	Remove contact lenses, if present and easy to do. Continue rinsing.
P340	Remove victim to fresh air and keep at rest in a position comfortable for breathing.
P341	If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P342	If experiencing respiratory symptoms:
P350	Gently wash with plenty of soap and water.
P351	Rinse cautiously with water for several minutes.
P352	Wash with plenty of soap and water.
P353	Rinse skin with water/shower.
P360	Rinse immediately contaminated clothing and skin with plenty of water before removing clothes.
P361	Remove/Take off immediately all contaminated clothing.
P362	Take off contaminated clothing and wash before reuse.
P363	Wash contaminated clothing before reuse.
P370	In case of fire:
P371	In case of major fire and large quantities:
P372	Explosion risk in case of fire.
P373	DO NOT fight fire when fire reaches explosives.
P374	Fight fire with normal precautions from a reasonable distance.
P376	Stop leak if safe to do so. Oxidising gases (section 2.4) 1
P377	Leaking gas fire: Do not extinguish, unless leak can be stopped safely.
P378
P380	Evacuate area.
P381	Eliminate all ignition sources if safe to do so.
P390	Absorb spillage to prevent material damage.
P391	Collect spillage. Hazardous to the aquatic environment
P301 + P310	IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician.
P301 + P312	IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell.
P301 + P330 + P331	IF SWALLOWED: Rinse mouth. Do NOT induce vomiting.
P302 + P334	IF ON SKIN: Immerse in cool water/wrap in wet bandages.
P302 + P350	IF ON SKIN: Gently wash with plenty of soap and water.
P303 + P361 + P353	IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower.
P304 + P312	IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell.
P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
P308 + P313	IF exposed or concerned: Get medical advice/attention.
P309 + P311	IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician.
P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
P333 + P313	IF SKIN irritation or rash occurs: Get medical advice/attention.
P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
P342 + P311	IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician.
P370 + P376	In case of fire: Stop leak if safe to Do so.
P370 + P378	In case of fire:
P370 + P380	In case of fire: Evacuate area.
P370 + P380 + P375	In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion.
P371 + P380 + P375	In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion.
Storage
Code	Phrase
P401
P402	Store in a dry place.
P403	Store in a well-ventilated place.
P404	Store in a closed container.
P405	Store locked up.
P406	Store in corrosive resistant/ container with a resistant inner liner.
P407	Maintain air gap between stacks/pallets.
P410	Protect from sunlight.
P411
P412	Do not expose to temperatures exceeding 50 oC/ 122 oF.
P413
P420	Store away from other materials.
P422
P402 + P404	Store in a dry place. Store in a closed container.
P403 + P233	Store in a well-ventilated place. Keep container tightly closed.
P403 + P235	Store in a well-ventilated place. Keep cool.
P410 + P403	Protect from sunlight. Store in a well-ventilated place.
P410 + P412	Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF.
P411 + P235	Keep cool.
Disposal
Code	Phrase
P501	Dispose of contents/container to ...
P502	Refer to manufacturer/supplier for information on recovery/recycling

Purity	Size	Price	VIP Price	USA Stock *0-1 Day	Global Stock *5-7 Days	Quantity
{[ item.p_purity ]}	{[ item.pr_size ]}	{[ getRatePrice(item.pr_usd, 1,1) ]} {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]}	{[ getRatePrice(item.pr_usd, 1,1) ]}	Inquiry {[ getRatePrice(item.pr_usd,item.pr_rate,item.mem_rate) ]} {[ getRatePrice(item.pr_usd,1,item.mem_rate) ]}	{[ item.pr_usastock ]}	Inquiry -	{[ item.pr_chinastock ]}	Inquiry -

Physical hazards
Code	Phrase
H200	Unstable explosive
H201	Explosive; mass explosion hazard
H202	Explosive; severe projection hazard
H203	Explosive; fire, blast or projection hazard
H204	Fire or projection hazard
H205	May mass explode in fire
H220	Extremely flammable gas
H221	Flammable gas
H222	Extremely flammable aerosol
H223	Flammable aerosol
H224	Extremely flammable liquid and vapour
H225	Highly flammable liquid and vapour
H226	Flammable liquid and vapour
H227	Combustible liquid
H228	Flammable solid
H229	Pressurized container: may burst if heated
H230	May react explosively even in the absence of air
H231	May react explosively even in the absence of air at elevated pressure and/or temperature
H240	Heating may cause an explosion
H241	Heating may cause a fire or explosion
H242	Heating may cause a fire
H250	Catches fire spontaneously if exposed to air
H251	Self-heating; may catch fire
H252	Self-heating in large quantities; may catch fire
H260	In contact with water releases flammable gases which may ignite spontaneously
H261	In contact with water releases flammable gas
H270	May cause or intensify fire; oxidizer
H271	May cause fire or explosion; strong oxidizer
H272	May intensify fire; oxidizer
H280	Contains gas under pressure; may explode if heated
H281	Contains refrigerated gas; may cause cryogenic burns or injury
H290	May be corrosive to metals
Health hazards
Code	Phrase
H300	Fatal if swallowed
H301	Toxic if swallowed
H302	Harmful if swallowed
H303	May be harmful if swallowed
H304	May be fatal if swallowed and enters airways
H305	May be harmful if swallowed and enters airways
H310	Fatal in contact with skin
H311	Toxic in contact with skin
H312	Harmful in contact with skin
H313	May be harmful in contact with skin
H314	Causes severe skin burns and eye damage
H315	Causes skin irritation
H316	Causes mild skin irritation
H317	May cause an allergic skin reaction
H318	Causes serious eye damage
H319	Causes serious eye irritation
H320	Causes eye irritation
H330	Fatal if inhaled
H331	Toxic if inhaled
H332	Harmful if inhaled
H333	May be harmful if inhaled
H334	May cause allergy or asthma symptoms or breathing difficulties if inhaled
H335	May cause respiratory irritation
H336	May cause drowsiness or dizziness
H340	May cause genetic defects
H341	Suspected of causing genetic defects
H350	May cause cancer
H351	Suspected of causing cancer
H360	May damage fertility or the unborn child
H361	Suspected of damaging fertility or the unborn child
H361d	Suspected of damaging the unborn child
H362	May cause harm to breast-fed children
H370	Causes damage to organs
H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

[ CAS No. 608142-27-4 ] {[proInfo.proName]}

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Product Details of [ 608142-27-4 ]

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Application In Synthesis of [ 608142-27-4 ]

[ 608142-27-4 ] Synthesis Path-Upstream 1~6

[ 608142-27-4 ] Synthesis Path-Downstream 1~26

Related Functional Groups of [ 608142-27-4 ]

Aryls

Ethers

Amines

Sulfones

Precautionary Statements-General

Prevention

Response

Storage

Disposal

Physical hazards

Health hazards

Environmental hazards

Inquiry

Related Functional Groups of
[ 608142-27-4 ]