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Chemical Structure| 608142-27-4 Chemical Structure| 608142-27-4

Structure of 608142-27-4

Chemical Structure| 608142-27-4

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Product Details of [ 608142-27-4 ]

CAS No. :608142-27-4
Formula : C12H19NO4S
M.W : 273.35
SMILES Code : O=S(C[C@H](N)C1=CC=C(OC)C(OCC)=C1)(C)=O
MDL No. :MFCD22643957
InChI Key :BXUJVINGXQGNFD-JTQLQIEISA-N
Pubchem ID :10195080

Safety of [ 608142-27-4 ]

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

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.

  • Downstream synthetic route of [ 608142-27-4 ]

[ 608142-27-4 ] Synthesis Path-Downstream   1~9

  • 2
  • N-(1-(3-ethoxy-4-methoxyphenyl)-2-(methylsulfonyl)ethyl)-2-methylpropane-2(R)-sulfinamide [ No CAS ]
  • [ 608141-42-0 ]
  • [ 608142-27-4 ]
YieldReaction ConditionsOperation 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).
  • 3
  • [ 1450657-31-4 ]
  • [ 608141-42-0 ]
  • [ 608142-27-4 ]
YieldReaction ConditionsOperation 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).
  • 4
  • [ 60758-86-3 ]
  • [ 608141-42-0 ]
  • [ 608142-27-4 ]
  • 5
  • C12H19NO4S*C10H10ClNO5 [ No CAS ]
  • [ 608141-42-0 ]
  • [ 608142-27-4 ]
YieldReaction ConditionsOperation 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%)
  • 7
  • [ 608142-27-4 ]
  • [ 608141-42-0 ]
  • 8
  • [ 60758-79-4 ]
  • [ 608141-42-0 ]
  • [ 608142-27-4 ]
  • 9
  • [ 121-32-4 ]
  • [ 608141-42-0 ]
  • [ 608142-27-4 ]
 

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