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[ CAS No. 142570-56-7 ] {[proInfo.proName]}

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Chemical Structure| 142570-56-7
Chemical Structure| 142570-56-7
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Product Details of [ 142570-56-7 ]

CAS No. :142570-56-7 MDL No. :MFCD14707528
Formula : C10H20N2O4 Boiling Point : -
Linear Structure Formula :- InChI Key :SFDSZSRXXGFFEH-UHFFFAOYSA-N
M.W : 232.28 Pubchem ID :10823469
Synonyms :

Safety of [ 142570-56-7 ]

Signal Word:Danger Class:4.1
Precautionary Statements:P240-P210-P241-P264-P280-P302+P352-P370+P378-P337+P313-P305+P351+P338-P362+P364-P332+P313 UN#:1325
Hazard Statements:H228-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 142570-56-7 ]

* 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 [ 142570-56-7 ]

[ 142570-56-7 ] Synthesis Path-Downstream   1~4

  • 1
  • [ 3303-84-2 ]
  • [ 6638-79-5 ]
  • [ 142570-56-7 ]
YieldReaction ConditionsOperation in experiment
100% Stage #1: 3-(tert-butyloxycarbonylamino)propionic acid With 4-methyl-morpholine; isobutyl chloroformate In dichloromethane at -15℃; for 0.25h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at -15 - 20℃; for 16h;
99% Stage #1: 3-(tert-butyloxycarbonylamino)propionic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 0.5h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With N-ethyl-N,N-diisopropylamine In dichloromethane 3 To a solution of Boc-β-alanine (12) (1.0 g, 5.28 mmol) in DCM (30 mL) was added N,N'-carbonyldiimidazole (856 mg, 5.81 mmol), followed by stirring at room temperature for 30 min. Diisopropylethylamine (1.0 mL, 5.81 mmol) and Weinreb amine (567 mg, 5.81 mmol) were added and the mixture stirred overnight. The solution was diluted with DCM (100 mL), washed with 5% citric acid (30 mL) and brine (30 mL), dried (MgSO4) and concentrated to obtain a colorless oil (13) (1.21 g, 99%). 1H NMR (400 MHz, CDCL3) δ5.22 (br s, 1H), 3.68 (s, 3H), 3.41 (m, 2H), 3.18 (s, 3H), 2.63 (m, 2H), 1.42 (s, 9H); MS (ESI+) m/z 133.29 (M+H+-boc).
95% With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -15 - 20℃; Inert atmosphere;
87% Stage #1: 3-(tert-butyloxycarbonylamino)propionic acid With 1,1'-carbonyldiimidazole In tetrahydrofuran at 20℃; for 4h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride With triethylamine In tetrahydrofuran for 2h;
75% Stage #1: 3-(tert-butyloxycarbonylamino)propionic acid With 1,1'-carbonyldiimidazole In dichloromethane at 20℃; for 1h; Stage #2: N,O-dimethylhydroxylamine*hydrochloride In dichloromethane at 20℃; for 16h;
74% With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane for 24h;
65% With 4-methyl-morpholine; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at -15℃; for 1.5h;
53% With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate In dichloromethane at 20℃; for 2h; 3-((tert-butoxycarbonyl)amino)propanoic acid (2 g), HATU (4.42 g), Huenig’s Base (4.62 mE) and N,O-dimethylhydroxylamine hydrochloride (1.134 g) were combined in DCM and stirred at RT for two hours. The reaction was poured into water and the organics were extracted. The organic layer was evaporated to yield crude yellow oil. The product was purified by column chromatography (50 g C-i 8, 10-70% MeCN/ Water). Fractions collect and concentrated to yield a yellow oil Yield: 1.3 g, 53% yield. Expected Mass:232, Observed M+i: 233.
With (benzotriazo-1-yloxy)tris(dimethylamino)phosphonium hexafluorophosphate; N-ethyl-N,N-diisopropylamine 1.) r.t., 5 min, 2.) CH2Cl2, r.t., 4.5 h; Yield given. Multistep reaction;
63.5 g With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In N,N-dimethyl-formamide at 0 - 20℃; for 5h; Compound vi To a stirred solution of 3-[[(tert-butoxy)carbonyl]amino]propanoic acid (v) (60 g, 317.11 mmol), N-methoxy-methylamine hydrochloride (37.12 g, 380.53 mmol) and TEA (80.22 g, 792.77 mmol) in DMF was added HOBT (47.13 g, 348.82 mmol) and EDC1 (121.58 g, 634.21 mmol) in portions at 0°C. The mixture was stirred for 5 h at 20°C before being diluted with water (2 L). The resulting mixture was extracted with EtOAc (3x800 mL). and the combined organic layers washed with water (3x800 mL), saturated brine (1 L), and dried over anhydrous Na2S04. After filtration, the filtrate was concentrated under reduced pressure and the residue purified by silica chromatography, elution gradient 0 to 30% EtOAc in petroleum ether to afford compound (vi) (63.5 g) as a light yellow oil. ESI-MS m/z = 233.2 [M+H]+.

Reference: [1]Blaney, Paul; Grigg, Ronald; Rankovic, Zoran; Thornton-Pett, Mark; Xu, Juan [Tetrahedron, 2002, vol. 58, # 9, p. 1719 - 1737]
[2]Current Patent Assignee: PRISM BIOLAB - US2004/14763, 2004, A1 Location in patent: Page 20
[3]Niphakis, Micah J.; Turunen, Brandon J.; Georg, Gunda I. [Journal of Organic Chemistry, 2010, vol. 75, # 20, p. 6793 - 6805]
[4]Barrios-Rivera, Jonathan; Xu, Yingjian; Wills, Martin [Organic Letters, 2019, vol. 21, # 18, p. 7223 - 7227]
[5]Zygalski, Lukas; Middel, Christoph; Harms, Klaus; Koert, Ulrich [Organic Letters, 2018, vol. 20, # 16, p. 5071 - 5074]
[6]Keurulainen, Leena; Vahermo, Mikko; Puente-Felipe, Margarita; Sandoval-Izquierdo, Elena; Crespo-Fernández, Benigno; Guijarro-López, Laura; Huertas-Valentín, Leticia; De Las Heras-Dueña, Laura; Leino, Teppo O.; Siiskonen, Antti; Ballell-Pages, Lluís; Sanz, Laura M.; Castañeda-Casado, Pablo; Jiménez-Díaz, M. Belén; Martínez-Martínez, María S.; Viera, Sara; Kiuru, Paula; Calderón, Félix; Yli-Kauhaluoma, Jari [Journal of Medicinal Chemistry, 2015, vol. 58, # 11, p. 4573 - 4580]
[7]Rossi, Matteo; Bang, Jeong-kyu; Mazur, Sharlyn; Iera, Jaclyn A.; Phillips, Darren C.; Zambetti, Gerard P.; Appella, Daniel H. [Bioorganic and Medicinal Chemistry Letters, 2009, vol. 19, # 9, p. 2429 - 2434]
[8]Current Patent Assignee: NOVARTIS AG; Novartis (w/o Sandoz) - US9359400, 2016, B2 Location in patent: Page/Page column 71
[9]Bitan, Gal; Muller, Dan; Kasher, Ron; Gluhov, Evgenia V.; Gilon, Chaim [Journal of the Chemical Society. Perkin transactions I, 1997, # 10, p. 1501 - 1510]
[10]Current Patent Assignee: GLAUKOS CORPORATION - WO2020/154673, 2020, A1 Location in patent: Page/Page column 80; 82
  • 3
  • [ 42471-59-0 ]
  • [ 142570-56-7 ]
  • [ 781675-82-9 ]
YieldReaction ConditionsOperation in experiment
59% Stage #1: 1-bromo-3-(methoxymethoxy)benzene With n-butyllithium In tetrahydrofuran; hexane at -78℃; for 0.5h; Stage #2: [2-(methoxy-methyl-carbamoyl)-ethyl]-carbamic acid tert-butyl ester In tetrahydrofuran; hexane at -18℃; for 1h; 17.1 1-Bromo-3-(methoxymethoxy)benzene (3.938 g, 18.14 mmol) prepared from 3-bromophenol by the method described in Shin-Jikken-Kagaku-Koza (New Experiment Chemistry Lecture) Vol. 14, p.568 (Maruzen, 1978) was dissolved in tetrahydrofuran (8 mL), and to the solution was gradually added a 1.56 mol/L solution of n-butyl lithium in hexane (12.2 mL, 19.0 mmol) under cooling at -78°C. Subsequently, to the mixture was added THF (16 mL), and then the mixture was stirred at the same temperature for 30 minutes. The reaction mixture was gradually added to tert-butyl [2-(N-methoxy-N-methylcarbamoyl)ethyl]carbamate (this compound is prepared by condensation of N-tert-butoxycarbonyl-β-alanine and N,O-dimethylhydroxylamine hydrochloride) (2.010 g, 8.653 mmol) dissolved in THF (10 mL) at -18°C. The mixture was stirred at the same temperature for 1 hour, then to the mixture was added water and saturated aqueous ammonium chloride, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate/n-hexane = 1/4) to give tert-butyl {3-[3-(methoxymethoxy)phenyl]-3-oxopropyl}carbamate (1.568 g, 59%). APCI-MS m/z 310 (M+H) +.
  • 4
  • [ 75-16-1 ]
  • [ 142570-56-7 ]
  • [ 54614-95-8 ]
YieldReaction ConditionsOperation in experiment
24.8 g In tetrahydrofuran; at 0℃; for 5h;Inert atmosphere; Methylmagnesium bromide 1M in THF (328 mL, 328.07 mmol) was added dropwise to a 0C stirred solution of compound (vi) (63.5 g, 273.38 mmol) in THF (1 L) under an argon atmosphere. The mixture was stirred for 5h at 0C before being quenched with aqueous NH4CI (1 L) and extracted with EtOAc (3x800 mL). The combined organic layers were washed with water (3x1 L), saturated brine (1 L) and dried over anhydrous Na2SC>4. After filtration, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography, elution gradient 0-15% EtOAc in petroleum ether to afford compound (vii) (24.8 g) as a colorless oil. ESI-MS m/z = 233.2 [M+2Na]+ 1HNMR: (400MHz, DMSO-r ) d, ppm 1.37-1.42 (m, 10H), 2.08-2.09 (d,3H), 2.50-2.57 (m,2H), 3.08-3.13 (m,2H), 6.75 (s,lH).
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