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Product Details of [ 600-22-6 ]

CAS No. :600-22-6 MDL No. :MFCD00008754
Formula : C4H6O3 Boiling Point : -
Linear Structure Formula :- InChI Key :CWKLZLBVOJRSOM-UHFFFAOYSA-N
M.W : 102.09 Pubchem ID :11748
Synonyms :

Calculated chemistry of [ 600-22-6 ]

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 2
Num. H-bond acceptors : 3.0
Num. H-bond donors : 0.0
Molar Refractivity : 22.83
TPSA : 43.37 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) : -6.92 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.25
Log Po/w (XLOGP3) : 0.0
Log Po/w (WLOGP) : -0.25
Log Po/w (MLOGP) : -0.5
Log Po/w (SILICOS-IT) : -0.02
Consensus Log Po/w : 0.09

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 2.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.34
Solubility : 46.6 mg/ml ; 0.456 mol/l
Class : Very soluble
Log S (Ali) : -0.46
Solubility : 35.2 mg/ml ; 0.345 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.22
Solubility : 61.9 mg/ml ; 0.607 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 600-22-6 ]

Signal Word:Danger Class:3
Precautionary Statements:P210-P403+P235 UN#:3272
Hazard Statements:H225 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 600-22-6 ]

* 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 [ 600-22-6 ]
  • Downstream synthetic route of [ 600-22-6 ]

[ 600-22-6 ] Synthesis Path-Upstream   1~14

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Reference: [1] Collection of Czechoslovak Chemical Communications, 1989, vol. 54, # 5, p. 1306 - 1310
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  • [ 19524-06-2 ]
  • [ 29681-42-3 ]
YieldReaction ConditionsOperation in experiment
32%
Stage #1: With sodium hydrogencarbonate In dichloromethane; water
Stage #2: With sulfuric acid; iron(II) sulfate In dichloromethane; water
Stage #3: With dihydrogen peroxide In dichloromethane; water at -10℃; for 0.25 h;
Methyl 4-bromopyridine-2-carboxylate (147) <n="201"/>A solution of 4-bromopyridine hydrochloride (595 mg, 3.06 mmol) in DCM(20 mL) was washed with aqueous NaHCO3 (2 x 20 mL), dried (MgSO4) and filtered. The filtrate was made up to 45 mL by the addition of more DCM, then water (3 mL) was added, followed by iron(II) sulphate heptahydrate (8.51 g, 30.6 mmol) and cone. H2SO4 (0.95 mL, 9.18 mmol). In a separate flask, methyl pyruvate (4.15 mL, 46 mmol) was treated with hydrogen peroxide (3.5 mL, 30.6 mmol, 30percent solution in water) at -10°C, then this solution was added to the DCM/water mixture at -10°C with vigorous stirring. After 15 minutes, the reaction was diluted with iced water (100 mL) and extracted into DCM (4 x 20 mL). The combined DCM phases were dried (MgSO4) and removed in vacuo. The title compound was obtained after sequential column chromatography (gradient elution - 10-40percent EtOAc in heptane with 0.5percent triethylamine, then repeating with 0-20percent EtOAc in heptane with 0.5percent triethylamine). Yield: 211 mg (32percent). LC/MS tv 0.98 min.MS(ES+) m/z 218, 216 (M+H).
32%
Stage #1: With water; sodium hydrogencarbonate In dichloromethane
Stage #2: With sulfuric acid; dihydrogen peroxide; iron(II) sulfate In dichloromethane; water at -10℃; for 0.25 h;
Methyl 4-bromopyridine-2-carboxylate (147); A solution of 4-bromopyridine hydrochloride (595 mg, 3.06 mmol) in DCM(20 mL) is washed with aqueous NaHCO3 (2 x 20 mL), dried (MgSO4) and filtered. The filtrate is made up to 45 mL by the addition of more DCM, then water (3 mL) is added, followed by iron(II) sulphate heptahydrate (8.51 g, 30.6 mmol) and cone. H2SO4 (0.95 mL, 9.18 mmol). In a separate flask, methyl pyruvate (4.15 mL, 46 mmol) is treated with hydrogen peroxide (3.5 mL, 30.6 mmol, 30percent solution in water) at -10°C, then this solution is added to the DCM/water mixture at -10°C with vigorous stirring. After 15 minutes, the reaction is diluted with iced water (100 mL) and extracted into DCM (4 x 20 mL). The combined DCM phases are dried(MgSO4) and removed in vacuo. The title compound is obtained after sequential column chromatography (gradient elution - 10-40percent EtOAc in heptane with 0.5percent triethylamine, then repeating with 0-20percent EtOAc in heptane with 0.5percent triethylamine). EPO <DP n="290"/>Yield: 211 mg (32percent). LC/MS tx 0.98 min. MS(ES+) m/z 218, 216 (M+H).
32%
Stage #1: With sodium hydrogencarbonate In dichloromethane; water
Stage #2: With sulfuric acid; dihydrogen peroxide; iron(II) sulfate In dichloromethane; water at -10℃; for 0.25 h;
Synthesis of Compound R5; Methyl 4-bromopyridine-2-carboxylate (147); A solution of 4-bromopyridine hydrochloride (595 mg, 3.06 mmol) in DCM(20 mL) is washed with aqueous NaHCO3 (2 x 20 mL), dried (MgSO4) and filtered. The filtrate is made up to 45 mL by the addition of more DCM, then water (3 mL) is added, followed by iron(II) sulphate heptahydrate (8.51 g, 30.6 mmol) and cone. H2SO4 (0.95 mL, 9.18 mmol). In a separate flask, methyl pyruvate (4.15 mL, 46 mmol) is treated with hydrogen peroxide (3.5 mL, 30.6 mmol, 30percent solution in water) at -10°C, then this solution is added to the DCM/water mixture at -10°C with vigorous stirring. After 15 minutes, the reaction is diluted with iced water (100 mL) and extracted into DCM (4 x 20 mL). The combined DCM phases are dried (MgSO4) and removed in vacuo. The title compound is obtained after sequential column chromatography (gradient elution - 10-40percent EtOAc in heptane with 0.5percent triethylamine, then repeating with 0-20percent EtOAc in heptane with 0.5percent triethylamine). EPO <DP n="290"/>Yield: 211 mg (32percent).LC/MS tx 0.98 min.MS(ES+) m/z 218, 216 (M+H).
Reference: [1] Patent: WO2007/89669, 2007, A2, . Location in patent: Page/Page column 199-200
[2] Patent: WO2008/57469, 2008, A1, . Location in patent: Page/Page column 288-289
[3] Patent: WO2008/57468, 2008, A1, . Location in patent: Page/Page column 288-289
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  • [ 1120-87-2 ]
  • [ 29681-42-3 ]
Reference: [1] Patent: WO2008/57497, 2008, A2, . Location in patent: Page/Page column 288-289
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  • [ 17392-83-5 ]
YieldReaction ConditionsOperation in experiment
88.2 % ee
Stage #1: at 25℃; for 0.25 h;
Stage #2: With hydrogen In tetrahydrofuran for 6 h;
Methyl pyruvate (51 mg; 0.50 mmol) was dissolved in a reaction vessel in anhydrous THF (3.0 mL) and degassed with argon for 15 minutes. Bis(1,5-cycloocta-diene)rhodium trifluoromethanesulfonate (2.3 mg; 5 μmol; 0.01 equiv) and ligand 4a from Example 1 (3.7 mg; 6 μmol; 0.012 equiv) were combined and argon-degassed anhydrous THF (2.0 mL) was added. This solution was stirred at 25° C. under argon for 15 minutes and then added to the solution of 2-acetamidocinnamic acid. The resulting solution was then flushed with hydrogen and pressurized to 0.69-1.38 bars gauge (10-20 psig) hydrogen. The reaction mixture was stirred for 8 hours to afford 90.2percent conversion to methyl (R)-lactate with 88.2percent ee as determined by chiral GC analysis. The analytical properties of methyl lactate were identical to an authentic sample.Chiral GC [Cyclosil-B (JW Scientific) 30 m.x.0.25 mm ID, film thickness 0.25 μm, 75° C. isothermal, 15 psig He]: t&R[methyl (R)-lactate] 7.75 min, tR[methyl (S)-lactate] 9.16 min. tR(methyl pyruvate) 5.16 min.
99.2 % ee With hydrogen In methanol at 50℃; for 2 h; Autoclave General procedure: All catalytic reactions were carried out at 50 C in 25 mL ofmethanol solvent in a stainless steel autoclave reactorequipped with a gas inlet and outlet, pressure gauge, mechanicalstirrer and temperature controller thermocouple. The systemwas controlled by computerized software and an electronicmotherboard unit. For each reaction, 70 mg (0.1 mmol ofcatalytically active Pt metal) of solid catalyst and 100 mmol ofsubstrate were used. The catalytic hydrogenation reaction wascarried out under 5 MPa of hydrogen and the reaction time wasfixed at 2 h. At the end of the catalytic runs, the reaction mixturewas analyzed by GC and the conversion was calculated onthe basis of the areas of the starting material and product usingcalibration curve calculations.
Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 14, p. 1941 - 1944
[2] Tetrahedron, 1999, vol. 55, # 25, p. 7787 - 7804
[3] Patent: US6906213, 2005, B1, . Location in patent: Page/Page column 15
[4] Angewandte Chemie - International Edition, 2011, vol. 50, # 21, p. 4913 - 4917
[5] Organic and Biomolecular Chemistry, 2011, vol. 9, # 11, p. 4070 - 4078
[6] Chinese Journal of Catalysis, 2015, vol. 36, # 4, p. 634 - 638
[7] RSC Advances, 2015, vol. 5, # 124, p. 102481 - 102487
[8] Chemical Communications, 2017, vol. 53, # 23, p. 3346 - 3349
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  • [ 27871-49-4 ]
  • [ 17392-83-5 ]
YieldReaction ConditionsOperation in experiment
33 % ee With hydrogen In methanol at 50℃; for 15 h; The hydrogenation reaction of methyl pyruvate was performed by the same method as in Example 38 except that the sulfonate catalyst was changed to Ru(OTf)[(S,S)-Tsdpen](p-cymene). As a result, (S)-methyl lactate with 33percent ee was produced in a yield of only 25percent.
76 % ee With hydrogen In methanol at 50℃; for 15 h; In a stainless steel autoclave, Cp*Ir(OTf)[(S,S)-Tsdpen] (1.7 mg, 2.0 μmol) was charged, followed by purging with argon. Then, 1 ml of methanol and methyl pyruvate (0.18 ml, 2.0 mmol) were charged, and the autoclave was pressurized with hydrogen, followed by ten times of purging. Then, hydrogen was charged to 30 atm to initiate reaction. After stirring at 50° C. for 15 hours, the reaction pressure was returned to normal pressure. 1HNMR and GC analysis of the product showed that (S)-methyl lactate with 76percent ee was quantitatively produced. The spectral data of the resultant alcohol compound was as follows:1HNMR (400 MHz, CDCl3) δ 1.42 (d, J=7 Hz, 3H, CH3), 3.10 (br, 1H, OH), 3.79 (s, 3H, OCH3), 4.30 (q, J=7 Hz, 1H, CHOH); GC (Chirasil-DEX CB; column temperature, 80° C.; injection temperature, 250° C.; detection temperature, 275° C.; helium pressure, 100 kPa); tR of (R)-methyl lactate, 3.11 minutes; tR of (S)-methyl lactate, 3.49 minutes.
53 % ee With hydrogen In methanol at 50℃; for 2 h; Autoclave General procedure: All catalytic reactions were carried out at 50 C in 25 mL ofmethanol solvent in a stainless steel autoclave reactorequipped with a gas inlet and outlet, pressure gauge, mechanicalstirrer and temperature controller thermocouple. The systemwas controlled by computerized software and an electronicmotherboard unit. For each reaction, 70 mg (0.1 mmol ofcatalytically active Pt metal) of solid catalyst and 100 mmol ofsubstrate were used. The catalytic hydrogenation reaction wascarried out under 5 MPa of hydrogen and the reaction time wasfixed at 2 h. At the end of the catalytic runs, the reaction mixturewas analyzed by GC and the conversion was calculated onthe basis of the areas of the starting material and product usingcalibration curve calculations.
56 % ee With bis(acetylacetonato)palladium(II); hydrogen; Cinchonidin In methanol; tolueneAutoclave General procedure: Hydrogenation reaction was performed in a Picoclave GlassUster cyclone 075 BUCHI autoclave. A solution of the precursor and the modifier: 0.0304 g (1×10–4 mol) of palladium acetylacetonate, ~10–4 mol of the modifier, 3 mL of toluene, and 19 mL of methanol was transferred to a 100 mL vessel being bubbled with hydrogen. The pale-yellow solution was stirred under hydrogen pressure of 5 atm during 30 min, then 0.5 mL of the substrate in 8 mL of methanol was added, and the “zero sample” was withdrawn. The mixture of hydrogenation products was then analyzed each 30 or 60 min using the chromato–mass spectrometer. Configuration of the prevailing enantiomer was determined by comparison with the reference data [43].

Reference: [1] Journal of the Chemical Society, Chemical Communications, 1992, # 23, p. 1738 - 1740
[2] Journal of the Chemical Society, Chemical Communications, 1994, # 21, p. 2431 - 2432
[3] Recueil des Travaux Chimiques des Pays-Bas, 1994, vol. 113, # 10, p. 465 - 474
[4] Journal of Catalysis, 1994, vol. 150, # 2, p. 321 - 328
[5] Synthesis, 1998, # 1, p. 45 - 55
[6] Tetrahedron Letters, 1998, vol. 39, # 14, p. 1941 - 1944
[7] Chemical Communications, 1998, # 14, p. 1451 - 1452
[8] Journal of Organic Chemistry, 1988, vol. 53, # 6, p. 1231 - 1238
[9] Journal of Organic Chemistry, 1985, vol. 50, # 9, p. 1384 - 1394
[10] Journal of the American Chemical Society, 1984, vol. 106, # 5, p. 1531 - 1533
[11] Journal of Organic Chemistry, 1994, vol. 59, # 11, p. 3064 - 3076
[12] Journal of the Chemical Society, Chemical Communications, 1995, # 6, p. 685 - 686
[13] Journal of Organic Chemistry, 1996, vol. 61, # 18, p. 6244 - 6251
[14] Chemical Communications, 1998, # 14, p. 1451 - 1452
[15] Journal of Organic Chemistry, 1990, vol. 55, # 26, p. 6328 - 6333
[16] Journal of the American Chemical Society, 1988, vol. 110, # 2, p. 629 - 631
[17] Journal of Organic Chemistry, 1994, vol. 59, # 11, p. 3064 - 3076
[18] Chemical Communications, 1998, # 14, p. 1451 - 1452
[19] Tetrahedron, 1999, vol. 55, # 25, p. 7787 - 7804
[20] Journal of the American Chemical Society, 1999, vol. 121, # 20, p. 4920 - 4921
[21] Journal of the American Chemical Society, 1999, vol. 121, # 20, p. 4920 - 4921
[22] Journal of Organic Chemistry, 1999, vol. 64, # 18, p. 6603 - 6608
[23] Tetrahedron Letters, 2000, vol. 41, # 16, p. 2867 - 2870
[24] Tetrahedron Letters, 2000, vol. 41, # 16, p. 2867 - 2870
[25] Journal of Catalysis, 2004, vol. 221, # 2, p. 653 - 656
[26] Journal of Organic Chemistry, 2005, vol. 70, # 5, p. 1872 - 1880
[27] Journal of the American Chemical Society, 2006, vol. 128, # 17, p. 5955 - 5965
[28] Canadian Journal of Chemistry, 2005, vol. 83, # 6-7, p. 903 - 908
[29] Synlett, 2006, # 8, p. 1169 - 1172
[30] Chemistry Letters, 1987, p. 855 - 858
[31] Chemistry Letters, 1987, p. 855 - 858
[32] Chemical Communications, 2003, # 15, p. 1926 - 1927
[33] Organic Letters, 2002, vol. 4, # 14, p. 2421 - 2424
[34] Tetrahedron Asymmetry, 2007, vol. 18, # 19, p. 2305 - 2312
[35] Patent: WO2004/78686, 2004, A1, . Location in patent: Page 20
[36] Patent: US2008/234525, 2008, A1, . Location in patent: Page/Page column 10
[37] Patent: US2008/234525, 2008, A1, . Location in patent: Page/Page column 10
[38] Patent: US2008/234525, 2008, A1, . Location in patent: Page/Page column 10
[39] Angewandte Chemie - International Edition, 2011, vol. 50, # 21, p. 4913 - 4917
[40] Dalton Transactions, 2011, vol. 40, # 13, p. 3325 - 3335
[41] Advanced Synthesis and Catalysis, 2014, vol. 356, # 9, p. 1943 - 1948
[42] Advanced Synthesis and Catalysis, 2014, vol. 356, # 9, p. 1943 - 1948
[43] Chinese Journal of Catalysis, 2015, vol. 36, # 4, p. 634 - 638
[44] RSC Advances, 2015, vol. 5, # 124, p. 102481 - 102487
[45] Advanced Synthesis and Catalysis, 2015, vol. 357, # 16-17, p. 3513 - 3520
[46] Russian Journal of General Chemistry, 2018, vol. 88, # 2, p. 199 - 207[47] Zh. Obshch. Khim., 2018, vol. 88, # 2, p. 219 - 227,9
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Reference: [1] Justus Liebigs Annalen der Chemie, 1949, vol. 564, p. 35
[2] Justus Liebigs Annalen der Chemie, 1951, vol. 571, p. 44,55
[3] Journal of Organic Chemistry, 1957, vol. 22, p. 82
[4] Zhurnal Obshchei Khimii, 1958, vol. 28, p. 69; engl. Ausg. S. 71
[5] Helvetica Chimica Acta, 1966, vol. 49, p. 168 - 174
[6] Patent: WO2016/40553, 2016, A1, . Location in patent: Page/Page column 25
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  • [ 149-73-5 ]
  • [ 10076-48-9 ]
YieldReaction ConditionsOperation in experiment
77% With sulfuric acid In methanol for 4 h; Reflux Methyl 2,2-dimethoxypropanoate
100 g (979 mmol) of methyl 2-oxopropanoate were admixed with 135 g (1273 mmol) of trimethyl orthoformate in 240 ml of methanol.
After addition of 0.96 g (9.79 mmol) of concentrated H2SO4, the mixture was heated to reflux for 4 h.
The solvent was distilled off within 2 h, and the crude product was cooled to 10° C. and added to a solution of 2.4 g of KOH in 1200 ml of water at 10° C.
After repeated extraction with diethyl ether, the product was dried over Na2SO4, filtered and concentrated.
The residue was distilled again. B.p. (10 mbar): 50-55° C. Yield: 118 g (77percent)
1H NMR (CDCl3): σ=1.53 (s, 3H,C-CH3), 3.29 (s, 6H, CH3-O-C-O-CH3), 3.82 (s, 3H,COOCH3).
Reference: [1] Journal of the American Chemical Society, 1983, vol. 105, # 7, p. 2021 - 2029
[2] Patent: US2015/245616, 2015, A1, . Location in patent: Paragraph 0189; 0190
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Reference: [1] Patent: WO2006/35915, 2006, A1, . Location in patent: Page/Page column 49-50
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YieldReaction ConditionsOperation in experiment
62% for 4 h; Reflux Svnthesis of S-Methoxy-pyrrolidine-S-carboxylic acid methyl ester Step 1 : Preparation of methyl α, α-dimethoxypropionate The procedure by Ernest Wenkert, et al. (JACS, 1983, 705, 2021 -2029) was followed. A solution of methyl pyruvate (44g), trimethyl orthoformate (62 ml), concentrated H2SO4 (0.2 ml) in MeOH (120 ml) was reluxed for 4 hours. In the next one hour period, solvent (about 80 ml) was distilled out. The reaction mixture was cooled to 10 0C, poured into a KOH solution (1 .2 g KOH in 600 ml water), and extracted with ether (3x). Combined ether extracts were washed with brine and dried (MgSO4). After concentration, the residue was distilled under vacuum to provide the acetal (8BH) (4Og, 62percent, 40-43C/1 torr).
Reference: [1] Patent: WO2009/105500, 2009, A1, . Location in patent: Page/Page column 215
[2] Journal of the Chemical Society, 1942, p. 521
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Reference: [1] Patent: EP1798218, 2007, A1,
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Reference: [1] Synthesis, 1983, # 3, p. 201 - 203
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Reference: [1] Tetrahedron Letters, 1998, vol. 39, # 47, p. 8563 - 8566
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  • [ 80-62-6 ]
  • [ 108365-85-1 ]
Reference: [1] Chemische Berichte, 1987, vol. 120, p. 1573 - 1580
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Reference: [1] Journal of Medicinal Chemistry, 2015, vol. 58, # 15, p. 6214 - 6224
[2] Patent: US2018/305353, 2018, A1, . Location in patent: Paragraph 0851-0853
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