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Chemical Structure| 880468-89-3
Chemical Structure| 880468-89-3
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Product Details of [ 880468-89-3 ]

CAS No. :880468-89-3 MDL No. :MFCD16620517
Formula : C16H24N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :ZEWWJSJMNBJIKR-CYBMUJFWSA-N
M.W : 308.37 Pubchem ID :46223141
Synonyms :

Calculated chemistry of [ 880468-89-3 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.5
Num. rotatable bonds : 10
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 83.27
TPSA : 76.66 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : No
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.0 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.84
Log Po/w (XLOGP3) : 1.66
Log Po/w (WLOGP) : 1.69
Log Po/w (MLOGP) : 1.25
Log Po/w (SILICOS-IT) : 1.84
Consensus Log Po/w : 1.86

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -2.34
Solubility : 1.41 mg/ml ; 0.00458 mol/l
Class : Soluble
Log S (Ali) : -2.88
Solubility : 0.403 mg/ml ; 0.00131 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.32
Solubility : 0.0148 mg/ml ; 0.0000479 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.09

Safety of [ 880468-89-3 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H332-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 880468-89-3 ]

* 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 [ 880468-89-3 ]
  • Downstream synthetic route of [ 880468-89-3 ]

[ 880468-89-3 ] Synthesis Path-Upstream   1~12

  • 1
  • [ 1253790-58-7 ]
  • [ 77-78-1 ]
  • [ 880468-89-3 ]
YieldReaction ConditionsOperation in experiment
96.28% With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 0 - 30℃; for 1.5 h; Put toluene at room temperature (4.8L) with Lacosamide stage II product (1kg), cooled to 0 °C, put sodium hydroxide solution 1 (0.54kg), tetrabutylammonium bromide (0.186 kg) with dimethyl sulfate (0.86 kg), heated to 30 °C, stir for 90 minutes. Extracted with toluene, put 5percent sodium bicarbonate solution, separate the organic phase. Put cyclohexane, stirred for 10 minutes and concentrated at 50 °C under reduced pressure for 2 hours. Drying to obtain lacosamide stage III. Yield of about 96.28percent.
75.8% With sodium hydroxide In dichloromethane; water at 4 - 25℃; Inert atmosphere 2.
(R)-boc-2-amino-N-benzyl-3-methoxy-propionamide (IV)
In a 4 L flask with overhead stirrer, thermometer, dropping funnel and under nitrogen were combined 120 g (R)-boc-2-amino-N-benzyl-3-hydroxy-propionamide (III) (0.407 mol) and 1 kg dichloromethane.
The reaction was cooled on ice to 4-8°C and 6.9 g tetrabutylammonium bisulfate (6.8 mmol) and 285 g of 20percent sodium hydroxide in water (0.475 mol) added.
To the reaction was then added 154 g (1.22 mol) dimethyl sulfate and the reaction stirred at 4-8 °C for 4 hours and overnight at 20-25 °C.
A sample showed greater than 98percent methylation of the starting (R)-boc-2-amino-N-benzyl-3-hydroxy-propionamide.
The reaction was quenched by additing 330 g of 25percent ammonium hydroxide solution in water plus a further 330 g water and stirred for 2 hours.
The phases were then separated and the aqueous phase extracted with 340 g dichloromethane.
The combined dichloromethane phases were washed with 450 ml water, then the dichloromethane was exchanged for tert-butyl methyl ether (MTBE) and the product crystallised from 345 ml MTBE at 4 °C overnight. The crystals were filtered and washed 2 times with 45 ml MTBE and dried to yield 95.3 g (75.8percent yield), HPLC purity = 98.6percent, ee >99percent ,1H NMR conforms.
75.8%
Stage #1: With tetra(n-butyl)ammonium hydrogensulfate; sodium hydroxide In dichloromethane; water at 4 - 25℃; Cooling with ice; Inert atmosphere
Stage #2: With ammonium hydroxide In dichloromethane; water
2. (R)-boc-2-amino-N-benzyl-3-methoxy-propionamide (IV)In a 4 L flask with overhead stirrer, thermometer, dropping funnel and under nitrogen were combined 120 g (R)-boc-2-amino-N-benzyl-3-hydroxy-propionamide (III) (0.407 mol) and 1 kg dichloromethane. The reaction was cooled on ice to 4-8° C. and 6.9 g tetrabutylammonium bisulfate (6.8 mmol) and 285 g of 20percent sodium hydroxide in water (0.475 mol) added. To the reaction was then added 154 g (1.22 mol) dimethyl sulfate and the reaction stirred at 4-8° C. for 4 hours and overnight at 20-25° C. A sample showed greater than 98percent methylation of the starting (R)-boc-2-amino-N-benzyl-3-hydroxy-propionamide. The reaction was quenched by additing 330 g of 25percent ammonium hydroxide solution in water plus a further 330 g water and stirred for 2 hours. The phases were then separated and the aqueous phase extracted with 340 g dichloromethane. The combined dichloromethane phases were washed with 450 ml water, then the dichloromethane was exchanged for tert-butyl methyl ether (MTBE) and the product crystallised from 345 ml MTBE at 4° C. overnight. The crystals were filtered and washed 2 times with 45 ml MTBE and dried to yield 95.3 g (75.8percent yield), HPLC purity=98.6percent, ee >99percent, 1H NMR conforms.
Reference: [1] Patent: CN106957239, 2017, A, . Location in patent: Paragraph 0036; 0045-0047
[2] Patent: EP2399901, 2011, A1, . Location in patent: Page/Page column 8
[3] Patent: US2011/319649, 2011, A1, . Location in patent: Page/Page column 5
[4] Patent: US2011/34731, 2011, A1, . Location in patent: Page/Page column 7
[5] Patent: WO2011/144983, 2011, A2, . Location in patent: Page/Page column 26-27
[6] Patent: WO2012/1710, 2012, A1, . Location in patent: Page/Page column 8; 12
[7] Patent: WO2013/24383, 2013, A1, . Location in patent: Paragraph 81; 82; 83
[8] Patent: US2013/102811, 2013, A1, . Location in patent: Paragraph 0043
[9] Patent: US2013/123537, 2013, A1, . Location in patent: Paragraph 0117
[10] Patent: WO2018/60781, 2018, A1, . Location in patent: Page/Page column 17-18
  • 2
  • [ 1253790-58-7 ]
  • [ 80-48-8 ]
  • [ 880468-89-3 ]
YieldReaction ConditionsOperation in experiment
80% With tetrabutylammomium bromide; potassium hydroxide In toluene at -1 - 2℃; Toluene (820 mL), Intermediate III (50 g), methyl p-toluenesulfonate (63.5 g),Tetrabutylammonium bromide (5.4 g) was added and the mixture was cooled with stirring to -1 to 2 ° C. Potassium hydroxide aqueous solution (40 g / 34 mL) was added at -1 to 2 ° C, and the addition was completed in about 5 minutes. The addition was complete, continue to control the temperature at -1 ~ 2 reaction 4 ~ 4.5 hours (TLC detection or HPLC control) to stop the reaction. After completion of the reaction, water (400 mL) was added to separate the layers. Organic layer followed by 5percent phosphoric acid, saturated sodium bicarbonate, water each200mL wash. Decompression 40 ~ 45 ° C The solvent was evaporated to give an oil, the reaction was used directly for the next step. HPLC purity 95percent, chiral Purity 99.1percent.
60.97g With tetrabutylammomium bromide; potassium hydroxide In water; toluene at 20℃; for 3 h; Toluene (330 mL) was added sequentially to the 1 L reaction flask,The compound of formula II (20.00 g, 68 mmol)P-toluenesulfonic acid methyl ester (63.50 g, 340 mmol),Tetrabutylammonium bromide (2.63 g, 8.16 mmol),Stir evenly,An aqueous solution of potassium hydroxide (16.00 g of potassium hydroxide + 16 mL of water) was added at room temperature,Plus complete, room temperature reaction 3 hours.Reaction completed, adding water (160mL), stirring 5min, standing stratification, liquid separation,Organic layer followed by 5percent phosphoric acid(80 mL), water (160 mL x 2), and the organic layer was concentrated at 55 ° C under reduced pressure. The solvent was evaporated to give 60.97 g of an oil.The product of this example was the same as in Example 1 by isolation and identification.
38.5 g With tetrabutylammomium bromide; sodium hydroxide In water at 20℃; for 3 h; To a 1L reaction flask were sequentially added toluene (330 mL), Compound II (20.00 g, 68 mmol), methyl p-toluenesulfonate (38.10 g, 204 mmol), tetrabutylammonium bromide (2.63 g, 8.16 mmol), Stir well, add aqueous sodium hydroxide solution (16.00g of sodium hydroxide + 16mL of water) at room temperature, complete the addition, and react at room temperature for 3 hours. After the reaction is complete, add water (160 mL), stir for 5 min, stand for layering, separate the liquid, and use 5percent phosphoric acid in order for the organic layer.(80 mL) and water (160 mL×2) were washed. The organic layer was concentrated under reduced pressure at 55° C., and the solvent was evaporated to give 38.5 g of an oil.
38.5 g With tetrabutylammomium bromide; sodium hydroxide In water; toluene at 20℃; for 3 h; Toluene (330 mL) was added sequentially to a 1L reaction flask,Compound II (20.00 g, 68 mmol),Methyl p-toluenesulfonate (38.10 g, 204 mmol),Tetrabutylammonium bromide (2.63 g, 8.16 mmol),Stir well,An aqueous solution of sodium hydroxide (16.00 g of sodium hydroxide + 16 mL of water) was added at room temperature.After the addition, the reaction was carried out at room temperature for 3 hours.After the reaction is complete, add water (160 mL) and stir for 5 min.Static stratification, liquid separation,The organic layer was successively washed with 5percent phosphoric acid (80 mL) and water (160 mL×2), and the organic layer was concentrated under reduced pressure at 55° C.After the solvent was distilled off, 38.5 g of an oil was obtained.

Reference: [1] Patent: CN106699605, 2017, A, . Location in patent: Paragraph 0043; 0044; 0046; 0048; 0049
[2] Patent: CN104892460, 2017, B, . Location in patent: Paragraph 0045; 0081; 0082; 0083; 0084; 0085-0092
[3] Patent: CN104892461, 2017, B, . Location in patent: Paragraph 0085; 0086; 0087
[4] Patent: CN105037209, 2017, B, . Location in patent: Sheet 0083; 0084; 0085
  • 3
  • [ 100-46-9 ]
  • [ 86123-95-7 ]
  • [ 880468-89-3 ]
YieldReaction ConditionsOperation in experiment
90%
Stage #1: With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -78℃; Inert atmosphere
Stage #2: at -78 - 20℃; for 1 h;
To a solution of acid (R)-9 (0.7 g, 3.2 mmol) in dry THF was added N-methylmorpholine (0.43 mL, 3.8 mmol) at -78 °C under an argon atmosphere. After 5 min, isobutyl chloroformate (0.5 mL, 3.8 mmol) was added and stirred for another 5 min. To this reaction mixture benzylamine (0.4 mL, 3.8 mmol) was added at -78 °C after which the reaction mixture was stirred at room temperature for 1 h. After completion of the reaction, the reaction mixture was filtered, and washed with ethylacetate. The solvent was removed under reduced pressure and the crude product was subjected to column chromatography (silica gel, petroleum ether/acetone, 85:15) to yield (R)-10 as a colorless solid (0.9 g, 90percent); mp 63-64 °C; (c 0.9, CHCl3); IR (CHCl3, cm-1): νmax 3683, 3431, 3020, 2931, 2401, 1714, 1523, 1496, 1368, 1165, 1119, 928, 758, 669; 1H NMR (200 MHz, CDCl3): δH 1.43 (s, 9H), 3.37 (s, 3H), 3.47-3.54 (dd, J = 9.2, 6.1 Hz, 1H), 3.82 (dd, J = 9.3, 3.7 Hz, 1H), 4.27 (m, 1H), 4.47 (d, J = 5.1 Hz, 1H), 5.41 (br s, 1H), 6.77 (m, 1H), 7.22-7.37 (m, 5H); 13C NMR (50 MHz, CDCl3): δC 170.3 (CO), 155.5 (CO), 137.9 (C), 128.7 (CH, 2 carbons), 127.5 (CH, 3 carbons), 80.4 (C), 72.1 (CH2), 59.1 (CH3), 54.0 (CH), 43.5 (CH2), 28.3 (CH3, 3 carbons); MS: m/z 331 [M+Na]+.
90% With 4-methyl-morpholine; isobutyl chloroformate In tetrahydrofuran at -78 - 30℃; for 1 h; Inert atmosphere Example-5
Synthesis of (R)-tert-butyl 1-(benzylamino)-3-methoxy-1-oxopropan-2-ylcarbamate (R)-9
To a solution of acid (R)-8 (0.7 g, 3.2 mmol) in dry THF was added N-methylmorpholine (0.43 mL, 3.8 mmol) at -78° C. under argon atmosphere.
After 5 min, isobutyl chloroformate (0.5 mL, 3.8 mmol) was added and stirred the content for another 5 min.
To this reaction mixture benzylamine (0.4 mL, 3.8 mmol) was added at -78° C. and allowed the reaction mixture to stir at 30° C. for 1 h.
After completion of the reaction, reaction mixture was filtered, washed with ethylacetate.
The solvent was removed under reduced pressure and the crude product was subjected to column chromatography (silica gel, petroleum ether/acetone, 85:15) to yield (R)-9 as colorless solid (0.9 g, 90percent).
m.p 63-64° C.; [α]25D=-20.5 (c 0.9, CHCl3); IR (CHCl3, cm-1): vmax 3683, 3431, 3020, 2931, 2401, 1714, 1523, 1496, 1368, 1165, 1119, 928, 758, 669; 1H NMR (200 MHz, CDCl3): δH 1.43 (s, 9H), 3.37 (s, 3H), 3.47-3.54 (dd, J=9.2, 6.1 Hz, 1H), 3.82 (dd, J=9.3, 3.7 Hz, 1H), 4.27 (m, 1H), 4.47 (d, J=5.1 Hz, 1H), 5.41 (bs, 1H), 6.77 (m, 1H), 7.22-7.37 (m, 5H); 13C NMR (50 MHz, CDCl3): δC 170.3 (CO), 155.5 (CO), 137.9 (C), 128.7 (CH, 2 carbons), 127.5 (CH, 3 carbons), 80.4 (C), 72.1 (CH2), 59.1 (CH3), 54.0 (CH), 43.5 (CH2), 28.3 (CH3, 3 carbons); MS: m/z 331 [M+Na]+.
90%
Stage #1: With 4-methyl-morpholine In tetrahydrofuran at -78℃; for 0.0833333 h; Inert atmosphere
Stage #2: With isobutyl chloroformate In tetrahydrofuran at -78 - 20℃; for 1 h; Inert atmosphere
To a solution of acid 5 (0.985 g, 4.49 mmol) in dry THF (10ml) was added N-methylmorpholine (0.6 mL, 5.39 mmol) at -78 °C under an argon atmosphere.After 5 min, isobutyl chloroformate (0.7 mL, 5.39 mmol)was added and stirred for another 5 min. To this reaction mixture benzyl amine (0.6 mL, 5.39 mmol) was added at -78 °C andthe reaction mixture was allowed to come up to room temperature and stirred foranother 1 h. After completion of the reaction (TLC), the reaction mixture wasfiltered through a pad of celite, and washed with ethyl acetate (20 mL). Thesolvent was removed under reduced pressure and the crude reaction mixture wassubjected to flash chromatography (CombiFlash Rf 200i, Teledyne Isco) using RediSep silica gel column (12 g) eluting with petroleum ether–EtOAc (3:2,isocratic) to yield 6as a white solid (1.24 g, 90percent); Rf0.35 (40percent EtOAc inpetroleum ether); mp 63-64 °C [Lit.63-64 °C3]; [α]D26 -24.3 (c 1.04, CHCl3) [Lit. [α]D26-20.5 (c 0.9, CHCl3)3]; IR (CHCl3) umax:3428, 3345, 3017, 2933, 2405, 1708, 1671, 1493, 1365, 1220, 1167, 1116, 1075,1025, 922, 860, 762, 668 cm-1; 1H NMR (200 MHz, CDCl3) δ: 7.40-7.19 (m, 5H), 6.78 (brs, 1H),5.55-5.33 (m, 1H), 4.48 (d, J = 4.3 Hz, 2H), 4.27 (brs, 1H), 3.84 (dd, J= 3.9, 9.2 Hz, 1H), 3.50 (dd, J = 6.2, 9.1 Hz, 1H), 3.36 (s, 3H), 1.43(s, 9H); 13C NMR (50 MHz,CDCl3) δ: 170.3,155.5, 138.0, 128.7, 127.5, 80.4, 72.1, 59.1, 43.5, 28.3; HRMS (ESI): m/z calcdfor C16H24N2O4Na [M + Na]+331.1628; found: 331.1612.
46.4% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 20℃; for 2 h; Cooling with ice Synthesis of (R)-N-Benzyl-2-Boc-amino-3-methoxypropionamide[0157] (R)-2-N-Boc-amino-3-methoxypropanoic acid (15.0 g, 68.4 mmol), phenylmethanamine (7.33 g, 68.4 mmol), and DMAP (4.17 g, 34.2 mmol) were dissolved in DCM (150 mL). The solution was cooled in an ice-bath and EDC (21 .21 g, 137 mmol) was added dropwise to the solution. Once addition was complete, the reaction mixture stirred at warmed to room temperature and stirred for two hours. Then DCM (200 ml) was added to the mixture. The DCM organic phase was washed with H20 (200 mL x 1 ), 0.5 N HC1 (200 mL x 2), 5percent sodium bicarbonate (200 mL χ 2) and water (200 mL x 2). The organic phase was dried over sodium sulfate, filtered, and solvent removed under reduced pressure. The desired product was obtained as a colorless semi-solid with a purity >95percent (9.8 g, 46.4percent). NMR (500 MHz, CDC13) δ 1.46 (s, 9H), 3.38 (s, 3H), 3.51 (m, 1H), 3.86 (d, 1 H), 4.30 (br., 1H), 4.50 (s, 2H), 5.42 (br., 1H), 6.74 (br., 1H), 7.28 (m, 3H), 7.35 (m, 2H). LC-MS (m/z) , calculated. 308.2, found 309.1 [M + H]+, 331.1 [M + Naf.

Reference: [1] Tetrahedron Asymmetry, 2011, vol. 22, # 12, p. 1353 - 1357
[2] Patent: US2014/12044, 2014, A1, . Location in patent: Paragraph 0074; 0075
[3] Tetrahedron Letters, 2015, vol. 56, # 42, p. 5802 - 5803
[4] Patent: WO2012/51551, 2012, A1, . Location in patent: Page/Page column 36-37
[5] Patent: WO2006/37574, 2006, A1, . Location in patent: Page/Page column 18
[6] Patent: WO2011/99033, 2011, A1, . Location in patent: Page/Page column 42
[7] Patent: WO2012/46245, 2012, A1, . Location in patent: Page/Page column 9
  • 4
  • [ 100-46-9 ]
  • [ 880468-89-3 ]
YieldReaction ConditionsOperation in experiment
100% at 0 - 5℃; for 0.5 h; The above prepared compound of formula III (30.3g, 0 . 100mol) in the dichloromethane solution 0-5°C, added benzylamine (10.7g, 0 . 100mol) methylen chloride (22 ml) solution. In 0-5 °C reaction 30 minutes with water (88 ml), 10percent sodium hydroxide solution (88 ml), 0.6mol/L hydrochloric acid (88 ml), water (88 ml) washing the reactant, is distilled under reduced pressure to dry obtains the type compound IV 30.8g (yield 100percent, HPLC purity 93.0percent, chiral purity 95.8percent).
Reference: [1] Patent: CN104030943, 2016, B, . Location in patent: Paragraph 0114; 0115
  • 5
  • [ 100-46-9 ]
  • [ 880468-89-3 ]
YieldReaction ConditionsOperation in experiment
90.4% at 20℃; for 3 h; A mixture of 2,4-dioxo-3-azaspiro[5.5]undecan-3-yl N-(tert-butoxycarbonyl)-O-methyl-d-serinate Ib (Scheme 5) (3.0g, 7.53mmol) and benzyl amine (0.97g, 9.05mmol) was vigorously stirred for 3h at ambient temperature. After completion of the reaction, methyl tert-butyl ether (20mL) was added and stirred at room temperature for 1h. The reaction mixture was filtered, and washed with methyl tert-butyl ether (5mL). The filtrate was washed with 5percent aq HCl solution (10mL), water (2×10mL), brine (10mL), dried over Na2SO4, and evaporated under reduced pressure. The crude product solidified while standing overnight at room temperature to yield tert-butyl (R)-(1-(benzylamino)-3-methoxy-1-oxopropan-2-yl) carbamate Ic as a colorless solid (2.1g, 90.4percent); mp 62–64°C (lit.23 63–64°C); [α]D25=−20.8 (c 0.9, CHCl3) [lit.23 −20.5]; 97.68percent purity by HPLC (Method-d, Table 1); eepercent: 99.44percent (Method-j, Table 1) [(R)-isomer Rt=7.65min; (S)-isomer Rt=8.51min]. IR (KBr, cm−1): vmax 3326, 3030, 2971, 2950, 2927, 2852, 2824, 1684, 1650, 1528, 1496, 1453, 1393, 1364, 1351, 1317, 1284, 1252, 1227, 1171, 1115, 1095, 1046, 1021, 919, 870, 750, 697, 652; 1H NMR (300MHz, CDCl3): δH 1.43 (s, 9H), 3.36 (s, 3H), 3.47–3.52 (dd, J=9.3, 6.3Hz, 1H), 3.82–3.86 (dd, J=9.3, 3.9Hz, 1H), 4.27 (br, 1H), 4.48 (br s, 2H), 5.41 (br, 1H), 6.74 (br, 1H), 7.24–7.35 (m, 5H); 13C NMR (75MHz, CDCl3): δC 169.3, 154.5, 137.0, 127.5, 126.4, 79.2, 71.1, 58.0, 53.0, 42.3, 27.2; MS: m/z 331 [M+Na]+.
Reference: [1] Tetrahedron Asymmetry, 2016, vol. 27, # 11-12, p. 487 - 491
  • 6
  • [ 24424-99-5 ]
  • [ 880468-89-3 ]
Reference: [1] Patent: WO2011/99033, 2011, A1,
[2] Patent: WO2012/1710, 2012, A1,
[3] Patent: WO2012/46245, 2012, A1,
[4] Patent: WO2012/46245, 2012, A1,
[5] Patent: US2013/102811, 2013, A1,
[6] Patent: WO2014/155264, 2014, A1,
[7] Patent: CN104030943, 2016, B,
[8] Patent: CN104030943, 2016, B,
[9] Patent: CN106957239, 2017, A,
[10] Patent: WO2018/60781, 2018, A1,
  • 7
  • [ 3262-72-4 ]
  • [ 880468-89-3 ]
Reference: [1] Patent: WO2011/99033, 2011, A1,
[2] Patent: WO2011/144983, 2011, A2,
[3] Patent: WO2012/1710, 2012, A1,
[4] Patent: WO2012/46245, 2012, A1,
[5] Patent: WO2012/46245, 2012, A1,
[6] Patent: WO2012/51551, 2012, A1,
[7] Patent: WO2013/24383, 2013, A1,
[8] Patent: US2013/102811, 2013, A1,
[9] Patent: US2013/123537, 2013, A1,
[10] Patent: WO2014/155264, 2014, A1,
[11] Patent: CN104030943, 2016, B,
[12] Patent: CN104030943, 2016, B,
[13] Patent: CN106957239, 2017, A,
[14] Patent: WO2018/60781, 2018, A1,
  • 8
  • [ 3262-72-4 ]
  • [ 100-46-9 ]
  • [ 880468-89-3 ]
Reference: [1] Patent: EP2399901, 2011, A1,
[2] Patent: US2011/319649, 2011, A1,
  • 9
  • [ 100-46-9 ]
  • [ 880468-89-3 ]
Reference: [1] Patent: WO2011/144983, 2011, A2,
[2] Patent: WO2013/24383, 2013, A1,
[3] Patent: US2013/123537, 2013, A1,
  • 10
  • [ 86123-95-7 ]
  • [ 880468-89-3 ]
Reference: [1] Patent: WO2014/155264, 2014, A1,
[2] Patent: CN104030943, 2016, B,
  • 11
  • [ 721928-19-4 ]
  • [ 880468-89-3 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 42, p. 5802 - 5803
  • 12
  • [ 108149-63-9 ]
  • [ 880468-89-3 ]
Reference: [1] Tetrahedron Letters, 2015, vol. 56, # 42, p. 5802 - 5803
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