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[ CAS No. 75-98-9 ] {[proInfo.proName]}

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3d Animation Molecule Structure of 75-98-9
Chemical Structure| 75-98-9
Chemical Structure| 75-98-9
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Product Details of [ 75-98-9 ]

CAS No. :75-98-9 MDL No. :MFCD00004194
Formula : C5H10O2 Boiling Point : -
Linear Structure Formula :((CH3)3C)COOH InChI Key :IUGYQRQAERSCNH-UHFFFAOYSA-N
M.W : 102.13 Pubchem ID :6417
Synonyms :

Calculated chemistry of [ 75-98-9 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 7
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.8
Num. rotatable bonds : 1
Num. H-bond acceptors : 2.0
Num. H-bond donors : 1.0
Molar Refractivity : 27.66
TPSA : 37.3 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -5.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.28
Log Po/w (XLOGP3) : 1.47
Log Po/w (WLOGP) : 1.12
Log Po/w (MLOGP) : 0.89
Log Po/w (SILICOS-IT) : 0.2
Consensus Log Po/w : 0.99

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.33
Solubility : 4.74 mg/ml ; 0.0464 mol/l
Class : Very soluble
Log S (Ali) : -1.86
Solubility : 1.41 mg/ml ; 0.0138 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.39
Solubility : 41.8 mg/ml ; 0.409 mol/l
Class : Soluble

Medicinal Chemistry

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

Safety of [ 75-98-9 ]

Signal Word:Danger Class:8
Precautionary Statements:P280-P303+P361+P353-P304+P340-P305+P351+P338-P310 UN#:3265
Hazard Statements:H302+H312-H314 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 75-98-9 ]

* 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 [ 75-98-9 ]
  • Downstream synthetic route of [ 75-98-9 ]

[ 75-98-9 ] Synthesis Path-Upstream   1~45

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  • [ 29943-42-8 ]
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Reference: [1] Bioorganic and Medicinal Chemistry, 2015, vol. 23, # 17, p. 6069 - 6077
  • 2
  • [ 3355-28-0 ]
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Reference: [1] Patent: EP1338595, 2003, A2,
  • 3
  • [ 387338-41-2 ]
  • [ 50-00-0 ]
  • [ 6950-82-9 ]
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Reference: [1] Chemistry - A European Journal, 2001, vol. 7, # 21, p. 4604 - 4612
  • 4
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YieldReaction ConditionsOperation in experiment
100 %Spectr. With 1-chloro-1-(dimethylamino)-2-methyl-1-propene In chloroform-d1 at 20℃; Inert atmosphere General procedure: Reactions were performed under dry argon atmosphere under magnetic stirring. In procedure A, the alcohol was introduced through a syringe into a 0.5-1 M solution of the α-haloenamine (usually 1.1 equiv) in freshly dried chloroform or dichloromethane or the corresponding deuterated solvents. The reactions were quite exothermic. When performed on a preparative scale, the alcoholwas added at 0 °C, and then the mixture was left at room temperaturefor 0.5-3 h. In procedure B, the α-haloenamine was introduced into a solution of alcohol in the same solvents at 0 °C. It was shown that both procedures gave identical results. In few cases involving the preparation of unstable halides, the halogenation was effected at lower temperature (see Scheme 3) for up to 4 h. Yields were determined after removal of the solvent either by 1H NMR using an added standard (usually benzene or toluene) or by GLC. In some cases the halides were purified by distillation or flash chromatography. The isolated yields were always very close to those measured by NMR or GLC. Most of the halogenation products obtained in this study were known compounds: their spectroscopic properties have been shown to be identical to those reported in the literature and will therefore not been reported here.
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[3] Russian Journal of Organic Chemistry, 1995, vol. 31, # 2, p. 166 - 170[4] Zhurnal Organicheskoi Khimii, 1995, vol. 31, # 2, p. 191 - 195
[5] Justus Liebigs Annalen der Chemie, 1874, vol. 173, p. 372
[6] Justus Liebigs Annalen der Chemie, 1874, vol. 173, p. 372
[7] Journal of the American Chemical Society, 1987, vol. 109, # 26, p. 8056 - 8066
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[11] Chemistry Letters, 1985, p. 701 - 704
[12] Acta Chemica Scandinavica, Series B: Organic Chemistry and Biochemistry, 1982, vol. 36, # 7, p. 467 - 474
[13] Synthetic Communications, 1982, vol. 12, # 14, p. 1139 - 1146
[14] Tetrahedron, 1991, vol. 47, # 34, p. 7091 - 7108
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[18] Patent: US4374067, 1983, A,
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[24] Tetrahedron, 2010, vol. 66, # 26, p. 4811 - 4815
[25] Journal of Medicinal Chemistry, 2010, vol. 53, # 10, p. 4177 - 4186
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[52] Organometallics, 2017, vol. 36, # 1, p. 18 - 21
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[54] Molecules, 2017, vol. 22, # 5,
[55] Patent: US2017/274362, 2017, A1, . Location in patent: Paragraph 0105
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[57] Chinese Chemical Letters, 2018, vol. 29, # 1, p. 191 - 193
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[64] Patent: TWI626233, 2018, B, . Location in patent: Paragraph 0182; 0185; 0188
  • 5
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Reference: [1] Tetrahedron, 1993, vol. 49, # 8, p. 1535 - 1540
  • 6
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  • [ 1538-75-6 ]
Reference: [1] Tetrahedron, 1993, vol. 49, # 8, p. 1535 - 1540
  • 7
  • [ 7719-09-7 ]
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Reference: [1] Journal of Medicinal Chemistry, 2009, vol. 52, # 22, p. 7236 - 7248
  • 8
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  • [ 877675-72-4 ]
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Reference: [1] Journal of the American Chemical Society, 2010, vol. 132, # 14, p. 5002 - 5003
  • 9
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Reference: [1] Journal of the American Chemical Society, 1938, vol. 60, p. 1326
[2] Chemical & Pharmaceutical Bulletin, 1984, vol. 32, # 4, p. 1273 - 1278
  • 10
  • [ 79-37-8 ]
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Reference: [1] Arkiv foer Kemi, 1949, vol. 1, p. 413,417
  • 11
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  • [ 70298-88-3 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 18, p. 4602 - 4605
  • 12
  • [ 462-08-8 ]
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  • [ 70298-88-3 ]
Reference: [1] Tetrahedron, 1988, vol. 44, # 12, p. 3501 - 3512
  • 13
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  • [ 70298-89-4 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 18, p. 4602 - 4605
  • 14
  • [ 4026-20-4 ]
  • [ 815-17-8 ]
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YieldReaction ConditionsOperation in experiment
90% With bismuth(III) nitrate; sodium hydroxide; oxygen In water at 95℃; for 2 h; A reaction vessel which is equipped with a stirrer, internal thermometer and gas feed and can be heated using a heating mantle is charged with 1.0 g of activated carbon (medicinal carbon) having a 5percent by weight palladium content, 0.024 g of Bi (NO3)3.5H2O, 100 ml of 3N sodium hydroxide solution and 13.2 g (0.1 mol) of 3,3-dimethyl-2-hydroxybutyric acid (DHBA).
After expelling air from the reaction vessel using oxygen, the starting mixture is heated to 95° C. and stirred at this temperature until, after approx. 2 hours, 0.0535 mol of oxygen (approx. 1300 ml at room temperature and ambient pressure) has been taken up.The oxygen feed and the stirrer are then switched off.
After filtering off the catalyst (it can be reused), the filtrate is adjusted to PH 7.5 at room temperature using 20percent hydrochloric acid, the amount of filtrate is determined and the 3,3-dimethyl-2-oxobutyric acid content in an aliquot is determined by differential pulse polarography (base electrolyte; acetate buffer solution).The determination was effected against a 3,3-dimethyl-2-oxobutyric acid solution of known content which was used as an internal standard in a repeat measurement on the same sample.The determination gave a 3,3-dimethyl-2-oxobutyric acid yield of 11.7 g (90percent of theory).
After acidifying the filtrate to PH 1, repeatedly extracting using ether and vaporizing the ether, approx. 0.7 g (7percent of theory) of trimethyl acetic acid could be detected in the extraction residue by gas chromatography in addition to 3,3-dimethyl-2-oxobutyric acid. _Examples 2-5 (Comparative Examples) [0053] As described in Example 1, 0.1 mol (13.2 g) of 3,3-dimethyl-2-hydroxybutyric acid (DHBA) is oxidized to 3,3-dimethyl-2-oxobutyric acid (DOBA) in sodium hydroxide solution using oxygen under atmospheric pressure over 1 g of noble metal/activated carbon catalyst. [0054] Table 1 reports the type of noble metal/carbon catalyst used, the type and amount of additive, the amount of sodium hydroxide solution used, the oxidation temperature, the amount of oxygen taken up, the time required to take up this amount of oxygen and the DOBA yield achieved which was determined by polarography. For comparison, the values of Example 1 are also listed in Table 1.
Reference: [1] Patent: US2004/30186, 2004, A1, . Location in patent: Page 3-4
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Reference: [1] Zhurnal Obshchei Khimii, 1948, vol. 18, p. 57[2] Chem.Abstr., 1948, p. 4905
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Reference: [1] Journal of Organic Chemistry, 1981, vol. 46, # 20, p. 3997 - 4000
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Reference: [1] Monatshefte fuer Chemie, 1889, vol. 10, p. 779[2] Monatshefte fuer Chemie, 1891, vol. 12, p. 356
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Reference: [1] Justus Liebigs Annalen der Chemie, 1903, vol. 327, p. 207
[2] Justus Liebigs Annalen der Chemie, 1903, vol. 327, p. 207
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Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 9, p. 2750 - 2755
[2] Dalton Transactions, 2018, vol. 47, # 34, p. 11942 - 11952
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Reference: [1] Synthetic Communications, 1984, vol. 14, # 9, p. 857 - 864
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YieldReaction ConditionsOperation in experiment
64%
Stage #1: With ammonium peroxydisulfate; sulfuric acid; silver nitrate In water at 70℃; for 1 h;
Synthesis of Compound J.1. A flask was charged with 3,6-dichloropyridazine (1.49 g, 0.01 mol, 1.0 equiv), silver nitrate (0.17 g, 0.001 mol, 0.1 equiv), water (30 mL), pivalic acid (3.57 g, 0.035 mol, 3.5 equiv), and sulfuric acid (1.6 mL, 0.03 mol, 3.0 equiv). The mixture was heated to 70° C. and a solution of ammonium persulfate (2.28 g, 0.01 mol, 1.0 equiv) in water (10 mL) was added dropwise over ten minutes. The reaction was stirred at 70° C. for one hour and then cooled to RT. The reaction mixture was poured into ice water and then adjusted to pH 8 with aqueous ammonium hydroxide. The aqueous mixture was extracted with CH2Cl2 (2.x.250 mL). The combined organic extracts were filtered through a cotton plug, washed with aqueous 1 N NaOH (70 mL), dried over anhydrous MgSO4 and concentrated under reduced pressure. Purification by flash column chromatography (20percent EtOAc/hexanes) afforded the title compound (1.32 g, 64percent) as a white solid. 1H NMR: (CDCl3, 400 MHz) δ: 7.5 (s, 1H), 1.5 (s, 9H); Rf=0.5 (80percent EtOAc/hexanes).
64% With ammonium peroxydisulfate; sulfuric acid; silver nitrate In water at 70℃; for 1 h; A flask was charged with 3,6-dichloropyridazine (1.49 g, 0.01 mol, 1.0 equiv), silver nitrate (0.17 g, 0.001 mol, 0.1 equiv), water (30 mL), pivalic acid (3.57 g, 0.035 mol, 3.5 equiv), and sulfuric acid (1.6 mL, 0.03 mol, 3.0 equiv). The mixture was heated to 70° C. and a solution of ammonium persulfate (2.28 g, 0.01 mol, 1.0 equiv) in water (10 mL) was added dropwise over ten minutes. The reaction was stirred at 70° C. for one hr and then cooled to RT. The reaction mixture was poured into ice water and then adjusted to pH 8 with aqueous ammonium hydroxide. The aqueous mixture was extracted with CH2Cl2 (2.x.250 mL). The combined organic extracts were filtered through a cotton plug, washed with aqueous 1 N NaOH (70 mL), dried over anhydrous MgSO4 and concentrated under reduced pressure. Purification by flash column chromatography (20percent EtOAc/hexanes) afforded the title compound (1.32 g, 64percent) as a white solid. 1H NMR: (CDCl3, 400 MHz) δ: 7.5 (s, 1 H), 1.5 (s, 9 H); Rf=0.5 (80percent EtOAc/hexanes).
Reference: [1] Patent: US2009/5359, 2009, A1, . Location in patent: Page/Page column 39
[2] Patent: US2009/36419, 2009, A1, . Location in patent: Page/Page column 84
[3] Journal of Medicinal Chemistry, 2005, vol. 48, # 23, p. 7089 - 7092
[4] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 20, p. 6030 - 6033
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YieldReaction ConditionsOperation in experiment
53% With silver nitrate In hexane; water a
3,6-Dichloro-4-(1,1-dimethylethyl)pyridazine
Concentrated sulphuric acid (53.6 ml, 1.0 mol) was added carefully to a stirred suspension of 3,6-dichloropyridazine (50.0 g, 0.34 mol) in water (1.25 l).
This mixture was then heated to 70° C. (internal temperature) before the addition of trimethylacetic acid (47.5 ml, 0.41 mol).
A solution of silver nitrate (11.4 g, 0.07 mol) in water (20 ml) was then added over approximately one minute.
This caused the reaction mixture to become milky in appearance.
A solution of ammonium persulphate (230 g, 1.0 mol) in water (0.63 l) was then added over 20-30 minutes.
The internal temperature rose to approximately 85° C.
During the addition the product formed as a sticky precipitate.
Upon complete addition the reaction was stirred for an additional 10 minutes, then allowed to cool to room temperature.
The mixture was then poured onto ice and basified with concentrated aqueous ammonia, with the addition of more ice as required to keep the temperature below 10° C.
The aqueous was extracted with dichloromethane (3*300 ml).
The combined extracts were dried (MgSO4), filtered and evaporated to give 55.8 g of crude product as an oil.
This was purified by silica gel chromatography using 0-15percent ethyl acetate in hexane as eluent to give 37.31 g (53percent) of the desired compound.
Data for the title compound: 1H NMR (360 MHz, d6-DMSO) δ1.50 (9H, s), 7.48 (1H, s); MS (ES+) m/e 205 [MH]+, 207 [MH]+.
Reference: [1] Patent: US6630471, 2003, B1,
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YieldReaction ConditionsOperation in experiment
87%
Stage #1: With chloroformic acid ethyl ester; triethylamine In tetrahydrofuran at 0℃; for 0.5 h;
Stage #2: With ammonium chloride In tetrahydrofuran; water at 0℃; for 0.5 h;
General procedure: To a colorless solution of 75mg (0.50mmol) of 3-phenylpropanoic acid 1a in 10mL of THF were added at 0°C 67μL (0.70mmol, 1.4equiv) of ClCO2Et and 209μL (1.5mmol, 3.0equiv) of Et3N.
After stirring for 30min at 0°C, 0.75 ml of a 1.0M aqueous solution of NH4Cl (0.75mmol, 1.5equiv) was added at 0°C to the colorless suspension.
The mixture was stirred for 30min at 0°C and 5mL of H2O was added to the resulted mixture.
The colorless clear solution was extracted with 30mL of EtOAc and the aqueous layer was extracted with 20mL of EtOAc.
The organic layers were combined, washed with 5mL of brine, and dried over anhydrous MgSO4.
The crude product was chromatographed on silica gel with EtOAc to afford 72mg (96percent yield) of 3-phenylpropanamide 2a. 4.2.4
Pivalamide 2d
44 mg (87percent); colorless solid; mp: 105-108 °C; 1H NMR (400 MHz, CDCl3): δ 1.23 (s, 9H, CH3 *3), 5.21 (br, 1H, NHA), 5.59 (br, 1H, NHB); 13C NMR (100 MHz, CDCl3): δ 27.7, 38.7, 181.6; IR (KBr, vmax/cm-1) = 3398 (CONH), 3205 (CONH), 2960 (CH3), 1653 (CON), 1624 (CON); HRMS (ESI-TOF): Calcd for C5H11NONa (M+Na)+: 124.0733, found: 124.0723
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Reference: [1] Journal of Organic Chemistry, 1992, vol. 57, # 10, p. 2925 - 2929
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  • [ 75-98-9 ]
Reference: [1] Angewandte Chemie - International Edition, 2013, vol. 52, # 8, p. 2239 - 2242[2] Angew. Chem., 2013, vol. 125, # 8, p. 2295 - 2298,4
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  • [ 65854-91-3 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 18, p. 4602 - 4605
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  • [ 106-47-8 ]
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  • [ 65854-91-3 ]
Reference: [1] Journal of the Indian Chemical Society, 2005, vol. 82, # 6, p. 564 - 568
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Reference: [1] Organic Letters, 2011, vol. 13, # 9, p. 2256 - 2259
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Reference: [1] Organic Letters, 2016, vol. 18, # 18, p. 4602 - 4605
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  • [ 56619-93-3 ]
Reference: [1] Organic Letters, 2016, vol. 18, # 18, p. 4602 - 4605
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  • [ 19455-23-3 ]
Reference: [1] Journal of the American Chemical Society, 2015, vol. 137, # 41, p. 13272 - 13281
[2] Tetrahedron, 1993, vol. 49, # 46, p. 10643 - 10654
[3] Russian Journal of Coordination Chemistry/Koordinatsionnaya Khimiya, 2018, vol. 44, # 8, p. 473 - 482[4] Koord. Khim., 2018, vol. 44, # 8, p. 473 - 482,10
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Reference: [1] Inorganica Chimica Acta, 2012, vol. 392, p. 192 - 198
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Reference: [1] Inorganic Chemistry, 2015, vol. 54, # 10, p. 4709 - 4723
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  • [ 86847-59-8 ]
Reference: [1] Synlett, 2013, vol. 24, # 20, p. 2695 - 2700
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  • [ 64214-60-4 ]
YieldReaction ConditionsOperation in experiment
88%
Stage #1: at 0℃; for 0.166667 h;
Stage #2: With phosphorus trichloride In toluene at 20 - 60℃; for 0.5 h;
General procedure: A solution of NHMe(OMe) (0.360 g, 6.0 mmol) and benzoic acid (0.244 g, 2.0 mmol) was stirred in dry toluene (10 mL) at 0 °C for 10 min. A solution of PCl3 (0.137 g, 1.0 mmol) in dry toluene (2 mL) was then added dropwise to the mixture. The mixture was warmed to r.t. slowly and then stirred at 60 °C for 0.5 h. When the reaction was complete (TLC monitoring), the mixture was cooled to r.t. The mixture was then quenched with sat. NaHCO3 soln (20 mL) and extracted with EtOAc (3 × 10 mL). The combined organic layers were dried (anhyd MgSO4). The solvent was removed in vacuo.The product was purified by column chromatography (silica gel, petroleum ether–EtOAc, 3:2) to give pure 3a as a colorless oil; yield: 320 mg (97percent).
Reference: [1] Synthesis (Germany), 2014, vol. 46, # 3, p. 320 - 330
[2] Journal of Organic Chemistry, 2004, vol. 69, # 25, p. 8984 - 8986
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Reference: [1] Bulletin of the Korean Chemical Society, 2010, vol. 31, # 1, p. 171 - 173
[2] Synthetic Communications, 2001, vol. 31, # 13, p. 2011 - 2019
  • 43
  • [ 1062512-43-9 ]
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  • [ 64214-60-4 ]
Reference: [1] Organic Letters, 2009, vol. 11, # 19, p. 4474 - 4477
  • 44
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  • [ 832715-99-8 ]
Reference: [1] Patent: WO2008/33858, 2008, A2, . Location in patent: Page/Page column 206
[2] Patent: WO2014/64131, 2014, A2, . Location in patent: Page/Page column 104; 105
[3] Patent: WO2008/33858, 2008, A2, . Location in patent: Page/Page column 206
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  • [ 158154-63-3 ]
YieldReaction ConditionsOperation in experiment
1.8 g With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine In N,N-dimethyl-formamide at 20 - 100℃; 3.10.2
Preparation of ethyl 5-(tert-butyl)-1,2,4-oxadiazole-3-carboxylate (949-4)
To a stirred solution of ethyl 2-(hydroxyamino)-2-iminoacetate (5.0 g, 37.8 mmol) in DMF (60 mL) were added pivalic acid (3.86 g, 37.8 mmol), 1-Ethyl-3-(3-dimethylaminopropyl)carbodiimide (EDCI) (7.97 g, 41.58 mmol), HOBt (6.12 g, 45.3 mmol) and DIPEA (19.7 mL, 113.4 mmol).
After being stirred at room temperature overnight, the reaction mixture was heated up to 100° C. for hr before cooled down to room temperature and partitioned between EA and H2O.
The layers were separated and the aqueous layer was extracted with EA (3*).
The combined organic layers were washed with brine and dried over Na2SO4.
The solvents were removed and the residue was purified by flash chromatography (silica gel, 10˜90percent ethyl acetate in petroleum ether) to provide ethyl 5-(tert-butyl)-1,2,4-oxadiazole-3-carboxylate (949-4) (1.8 g, 24percent) as a yellow solid. LC-MS: ESI m/z (M+1)=199.36.
Reference: [1] Patent: US2018/194762, 2018, A1, . Location in patent: Paragraph 0810
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