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[ CAS No. 70-47-3 ] {[proInfo.proName]}

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Chemical Structure| 70-47-3
Chemical Structure| 70-47-3
Structure of 70-47-3 * Storage: {[proInfo.prStorage]}
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Product Details of [ 70-47-3 ]

CAS No. :70-47-3 MDL No. :MFCD00064401
Formula : C4H8N2O3 Boiling Point : -
Linear Structure Formula :- InChI Key :DCXYFEDJOCDNAF-REOHCLBHSA-N
M.W : 132.12 Pubchem ID :6267
Synonyms :
L-Asparagine;(-)-Asparagine;Agedoite;Altheine;Asparagine;NSC 82391;(S)-Asparagine;α-Aminosuccinic Acid;alpha-aminosuccinamic acid;2-Aminosuccinamic acid;Asparamide;Asn
Chemical Name :H-Asn-OH

Calculated chemistry of [ 70-47-3 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.5
Num. rotatable bonds : 3
Num. H-bond acceptors : 4.0
Num. H-bond donors : 3.0
Molar Refractivity : 28.73
TPSA : 106.41 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) : -9.53 cm/s

Lipophilicity

Log Po/w (iLOGP) : -0.26
Log Po/w (XLOGP3) : -3.41
Log Po/w (WLOGP) : -1.73
Log Po/w (MLOGP) : -3.99
Log Po/w (SILICOS-IT) : -1.73
Consensus Log Po/w : -2.22

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 3.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : 1.69
Solubility : 6430.0 mg/ml ; 48.7 mol/l
Class : Highly soluble
Log S (Ali) : 1.75
Solubility : 7480.0 mg/ml ; 56.6 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : 1.1
Solubility : 1650.0 mg/ml ; 12.5 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.72

Safety of [ 70-47-3 ]

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

Application In Synthesis of [ 70-47-3 ]

* 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 [ 70-47-3 ]
  • Downstream synthetic route of [ 70-47-3 ]

[ 70-47-3 ] Synthesis Path-Upstream   1~57

  • 1
  • [ 70-47-3 ]
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Reference: [1] Journal of the American Chemical Society, 1959, vol. 81, p. 174
  • 2
  • [ 108-31-6 ]
  • [ 3130-87-8 ]
  • [ 70-47-3 ]
Reference: [1] Chemische Berichte, 1896, vol. 29, p. 2070[2] Gazzetta Chimica Italiana, 1897, vol. 27 I, p. 146
[3] Gazzetta Chimica Italiana, 1886, vol. 16, p. 278[4] Gazzetta Chimica Italiana, 1887, vol. 17, p. 185
[5] Chemische Berichte, 1886, vol. 19, p. 1694[6] Gazzetta Chimica Italiana, 1887, vol. 17, p. 127,186
  • 3
  • [ 21860-86-6 ]
  • [ 3130-87-8 ]
  • [ 70-47-3 ]
Reference: [1] Gazzetta Chimica Italiana, 1886, vol. 16, p. 278[2] Gazzetta Chimica Italiana, 1887, vol. 17, p. 185
[3] Gazzetta Chimica Italiana, 1887, vol. 17, p. 127,188[4] Gazzetta Chimica Italiana, 1888, vol. 18, p. 460
[5] Chemische Berichte, 1886, vol. 19, p. 1694[6] Gazzetta Chimica Italiana, 1887, vol. 17, p. 127,186
  • 4
  • [ 70-47-3 ]
  • [ 3130-87-8 ]
Reference: [1] Zeitschrift fuer Naturforschung, Teil B: Anorganische Chemie, Organische Chemie, 1983, vol. 38, # 10, p. 1281 - 1291
  • 5
  • [ 71989-16-7 ]
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Reference: [1] Amino Acids, 2014, vol. 46, # 2, p. 367 - 374
  • 6
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Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 30, p. 4149 - 4151
  • 7
  • [ 16856-13-6 ]
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Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, # 11, p. 2811 - 2814
  • 8
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Reference: [1] Chemical & Pharmaceutical Bulletin, 1987, vol. 35, # 7, p. 2994 - 3001
  • 9
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YieldReaction ConditionsOperation in experiment
51% With triethylamine In dichloromethane EXAMPLE 61
L-Asparagine, N-[1-(2-Adamantan-1-yl-2-Oxoethyl)-L-Prolyl] Benzylamide
Using the procedure described previously, a heterogeneous solution of 1-(2-adamantan-1-yl-2-oxoethyl) L-proline (152 mg, 0.52 mmol, 1.0 eq), L-asparagine N-benzylamide (231 mg, 1.04 mmol, 2.0 eq) and dichloromethane (1.5 mL), was treated with triethylamine (436 uL, 3.1 mmol, 6.0 eq), and a 50percent solution of 1-n-propylphosphonic acid cyclic anhydride in dichloromethane (663 uL, 1.04 mL, 2.0 eq), to provide 130.7 mg (51percent) of L-asparagine, N-[1-(2-adamantan-1-yl-2-oxoethyl)-L-prolyl] benzylamide as a white foam.
Rf (10percent MeOH in dichloromethane)=0.41
Reference: [1] Patent: US5686424, 1997, A,
  • 10
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  • [ 5241-58-7 ]
Reference: [1] Chemistry - A European Journal, 2000, vol. 6, # 21, p. 3906 - 3913
  • 11
  • [ 22849-01-0 ]
  • [ 70-47-3 ]
  • [ 63-91-2 ]
Reference: [1] Chemistry - A European Journal, 2000, vol. 6, # 21, p. 3906 - 3913
  • 12
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  • [ 57-13-6 ]
  • [ 70-47-3 ]
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Reference: [1] Chemistry - A European Journal, 2009, vol. 15, # 17, p. 4411 - 4418
  • 13
  • [ 3130-87-8 ]
  • [ 2058-58-4 ]
  • [ 70-47-3 ]
Reference: [1] Angewandte Chemie - International Edition, 2018, vol. 57, # 27, p. 8120 - 8124[2] Angew. Chem., 2018, vol. 130, p. 8252 - 8256,5
[3] Journal of the American Chemical Society, 1981, vol. 103, # 5, p. 1249 - 1251
[4] Journal of the American Chemical Society, 1981, vol. 103, # 5, p. 1251 - 1252
[5] Journal of the American Chemical Society, 1982, vol. 104, # 17, p. 4610 - 4617
[6] Analytical Chemistry, 2001, vol. 73, # 22, p. 5499 - 5508
[7] Chinese Journal of Chemistry, 2017, vol. 35, # 7, p. 1037 - 1042
[8] Chemistry - An Asian Journal, 2018, vol. 13, # 19, p. 2812 - 2817
  • 14
  • [ 1593896-98-0 ]
  • [ 57-48-7 ]
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Reference: [1] Organic Letters, 2014, vol. 16, # 9, p. 2414 - 2417
  • 15
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  • [ 473-81-4 ]
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Reference: [1] Organic Letters, 2014, vol. 16, # 9, p. 2414 - 2417
  • 16
  • [ 16473-76-0 ]
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  • [ 26117-27-1 ]
Reference: [1] Journal of the American Chemical Society, 1989, vol. 111, # 16, p. 6354 - 6364
  • 17
  • [ 108-31-6 ]
  • [ 3130-87-8 ]
  • [ 70-47-3 ]
Reference: [1] Chemische Berichte, 1896, vol. 29, p. 2070[2] Gazzetta Chimica Italiana, 1897, vol. 27 I, p. 146
[3] Gazzetta Chimica Italiana, 1886, vol. 16, p. 278[4] Gazzetta Chimica Italiana, 1887, vol. 17, p. 185
[5] Chemische Berichte, 1886, vol. 19, p. 1694[6] Gazzetta Chimica Italiana, 1887, vol. 17, p. 127,186
  • 18
  • [ 21860-86-6 ]
  • [ 3130-87-8 ]
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Reference: [1] Gazzetta Chimica Italiana, 1886, vol. 16, p. 278[2] Gazzetta Chimica Italiana, 1887, vol. 17, p. 185
[3] Gazzetta Chimica Italiana, 1887, vol. 17, p. 127,188[4] Gazzetta Chimica Italiana, 1888, vol. 18, p. 460
[5] Chemische Berichte, 1886, vol. 19, p. 1694[6] Gazzetta Chimica Italiana, 1887, vol. 17, p. 127,186
  • 19
  • [ 56-41-7 ]
  • [ 77287-34-4 ]
  • [ 56-45-1 ]
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  • [ 471-46-5 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 2014, vol. 87, # 11, p. 1208 - 1215
  • 20
  • [ 56-41-7 ]
  • [ 77287-34-4 ]
  • [ 56-45-1 ]
  • [ 70-47-3 ]
  • [ 56-40-6 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 2014, vol. 87, # 11, p. 1208 - 1215
  • 21
  • [ 4033-40-3 ]
  • [ 70-47-3 ]
Reference: [1] Bioscience, Biotechnology and Biochemistry, 2009, vol. 73, # 9, p. 1940 - 1947
  • 22
  • [ 2304-96-3 ]
  • [ 70-47-3 ]
Reference: [1] Zeitschrift für Naturforschung. Teil B: Chemie, Biochemie, Biophysik, Biologie, 1959, vol. 14 B, p. 472 - 473
[2] Gazzetta Chimica Italiana, 1958, vol. 88, p. 9,12
[3] Journal of Molecular Catalysis B: Enzymatic, 2012, vol. 84, p. 22 - 26
  • 23
  • [ 29880-25-9 ]
  • [ 70-47-3 ]
  • [ 29880-25-9 ]
  • [ 29880-25-9 ]
Reference: [1] Monatshefte fur Chemie, 2000, vol. 131, # 6, p. 667 - 672
  • 24
  • [ 56-84-8 ]
  • [ 70-47-3 ]
Reference: [1] Journal of Chemical Thermodynamics, 2000, vol. 32, # 9, p. 1077 - 1090
[2] Biochemistry, 2010, vol. 49, # 43, p. 9391 - 9401
  • 25
  • [ 3130-87-8 ]
  • [ 101-41-7 ]
  • [ 2058-58-4 ]
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Reference: [1] Tetrahedron Asymmetry, 2006, vol. 17, # 2, p. 245 - 251
  • 26
  • [ 111-26-2 ]
  • [ 78641-70-0 ]
  • [ 70-47-3 ]
  • [ 74197-48-1 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1984, vol. 57, # 7, p. 1961 - 1965
  • 27
  • [ 56-84-8 ]
  • [ 56-85-9 ]
  • [ 70-47-3 ]
  • [ 56-86-0 ]
Reference: [1] Bioorganic Chemistry, 2004, vol. 32, # 2, p. 63 - 75
  • 28
  • [ 687-29-6 ]
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Reference: [1] Chemische Berichte, 1957, vol. 90, p. 1879,1890
  • 29
  • [ 3130-87-8 ]
  • [ 70-47-3 ]
Reference: [1] Comptes Rendus Hebdomadaires des Seances de l'Academie des Sciences, 1959, vol. 248, p. 3722
  • 30
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  • [ 70-47-3 ]
Reference: [1] Journal of the Chemical Society, 1951, p. 2976
  • 31
  • [ 2058-58-4 ]
  • [ 70-47-3 ]
Reference: [1] Advanced Synthesis and Catalysis, 2011, vol. 353, # 13, p. 2431 - 2438
  • 32
  • [ 1999-33-3 ]
  • [ 70-47-3 ]
  • [ 56-40-6 ]
Reference: [1] New Journal of Chemistry, 2016, vol. 40, # 2, p. 976 - 984
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  • [ 56-45-1 ]
  • [ 70-47-3 ]
  • [ 56-40-6 ]
  • [ 71-00-1 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1985, vol. 33, # 8, p. 3205 - 3217
  • 34
  • [ 98115-12-9 ]
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Reference: [1] Chemical and Pharmaceutical Bulletin, 1986, vol. 34, # 8, p. 3506 - 3509
  • 35
  • [ 1206792-25-7 ]
  • [ 70-47-3 ]
  • [ 6893-26-1 ]
Reference: [1] Biochemistry, 2010, vol. 49, # 3, p. 611 - 622
  • 36
  • [ 21860-86-6 ]
  • [ 7664-41-7 ]
  • [ 2058-58-4 ]
  • [ 70-47-3 ]
Reference: [1] Gazzetta Chimica Italiana, 1887, vol. 17, p. 127,188[2] Gazzetta Chimica Italiana, 1888, vol. 18, p. 460
[3] Justus Liebigs Annalen der Chemie, 1871, vol. 157, p. 28
[4] Gazzetta Chimica Italiana, 1888, vol. 18, p. 471,478[5] Gazzetta Chimica Italiana, 1888, vol. 18, p. 476
  • 37
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  • [ 2058-58-4 ]
  • [ 70-47-3 ]
Reference: [1] Chemische Berichte, 1896, vol. 29, p. 2070[2] Gazzetta Chimica Italiana, 1897, vol. 27 I, p. 146
[3] Gazzetta Chimica Italiana, 1887, vol. 17, p. 175,229
  • 38
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  • [ 7664-41-7 ]
  • [ 2058-58-4 ]
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Reference: [1] Gazzetta Chimica Italiana, 1887, vol. 17, p. 230[2] Gazzetta Chimica Italiana, 1889, vol. 19, p. 422
[3] Gazzetta Chimica Italiana, 1887, vol. 17, p. 127,188[4] Gazzetta Chimica Italiana, 1888, vol. 18, p. 460
  • 39
  • [ 108-31-6 ]
  • [ 7664-41-7 ]
  • [ 2058-58-4 ]
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Reference: [1] Chemische Berichte, 1896, vol. 29, p. 2070[2] Gazzetta Chimica Italiana, 1897, vol. 27 I, p. 146
  • 40
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  • [ 5487-35-4 ]
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Reference: [1] Naturwissenschaften, 1956, vol. 43, p. 447
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YieldReaction ConditionsOperation in experiment
91% With sodium carbonate In 1,4-dioxane; water at 20℃; L-asparagine (15 g, 0.113 mol, LEQ.) and sodium carbonate (12 g, 0.113 mol) were dissolved in water (225 ML) and 1, 4-dioxane (225 ml) at r. T.. To this solution, di-tert-butyl-dicarbonate (30 g, 0.137 mol, 1.2 eq. ) was added and the mixture was stirred overnight. The solvent was evaporated under reduced pressure till 1,4-dioxane was distilled and the pH adjusted to 2 with HCI 37percent to give a white solid that was filtered, washed with water and dried. Yield 91percent. 24g. Analytical data: m. p. 175°C-180°C (lit. 175°C). 'H NMR (DMSO-D6) 12.5 (1H, br); 7.31 (1H, BR) ; 6.91 (1H, br); 6.87 (1H, d, J=8. 4 Hz); 4.23 (1H, q, J=7. 7 HZ) ; 2.56-2. 36 (2H, M) ; 1.38 (9H, s).
91%
Stage #1: With sodium carbonate In 1,4-dioxane; water at 20℃;
Stage #2: With hydrogenchloride In water
L-asparagine (15 g, 0.113 mol, 1 eq.) and sodium carbonate (12 g, 0.113 mol) were dissolved in water (225 ml) and 1,4-dioxane (225 ml) at r.t.
To this solution, di-tert-butyl-dicarbonate (30 g, 0.137 mol, 1.2 eq.) was added and the mixture was stirred overnight.
The solvent was evaporated under reduced pressure until 1,4-dioxane was distilled and the pH adjusted to 2 with HCl 37percent to give a white solid that was filtered, washed with water and dried.
Yield 91percent. 24 g.
Analytical data: m.p. 175° C.-180° C. (lit. 175° C.).
1H NMR (DMSO-d6) 12.5 (1H, br); 7.31 (1H, br); 6.91 (1H, br); 6.87 (1H, d, J=8.4 Hz); 4.23 (1H, q, J=7.7 Hz); 2.56-2.36 (2H, m); 1.38 (9H, s).
64% With sodium hydroxide In 1,4-dioxane; water at 10 - 20℃; General procedure: To a solution containing L-asparagine monohydrate (1a) (15 g, 0.10 mol) in a mixture of 1 M sodium hydroxide (100 mL) and water (180 mL) was added a solution containing di-t-butyloxydicarbonate (24 g, 0.11 mol) in 1,4-dioxane (170 mL) dropwise with stirring at 10 °C. After overnight stirring at room temperature, the reaction mixture was evaporated in vacuo to anoily product, which was cooled and acidified to pH 2 with 10 percent potassium hydrogen sulfate to give a precipitate. The precipitate was filtered, washed with water and recrystallizedwith 500 mL ethanol to give 14.8 g of crystals (64 percent). m.p.177-179 °C (lit. 20) 181-182). 1H NMR (DMSO-d6): d = 1.38ppm (9H, s, CH3), 2.09 (1H, s, NH), 2.48 (2H, d, CH2), 4.22(1H, q, CH), 6.88 (2H, d, NH2). IR (KBr, nmax, cm-1): 1720(COOH), 1690 (amide I), 1663 (amide II (side chain)), 1591(amide II (side chain)), 1535 (amide II). Elemental analysis:Calcd. for C9H16N2O5: C, 46.54; H, 6.94; N, 12.07 percent. Found:C, 46.70; H, 7.05; N, 11.99 percent. [a]D15-7.8° (c = 1.22, DMF) (lit.21) [aD]20 -7.8 (c = 1, DMF)).
Reference: [1] Patent: WO2005/21558, 2005, A2, . Location in patent: Page/Page column 214
[2] Patent: US2006/189806, 2006, A1, . Location in patent: Page/Page column 38
[3] Bioorganic and Medicinal Chemistry, 1998, vol. 6, # 8, p. 1185 - 1208
[4] Angewandte Chemie - International Edition, 2007, vol. 46, # 14, p. 2470 - 2477
[5] Organic Syntheses, 1985, vol. 63, p. 160 - 160
[6] Journal of Peptide Science, 2017, vol. 23, # 3, p. 202 - 214
[7] Bioorganic and Medicinal Chemistry, 2006, vol. 14, # 19, p. 6586 - 6592
[8] Asian Journal of Chemistry, 2014, vol. 26, # 19, p. 6541 - 6548
[9] Chemistry of Natural Compounds, 1979, vol. 15, p. 471 - 476[10] Khimiya Prirodnykh Soedinenii, 1979, vol. 15, p. 543 - 548
[11] Journal of Organic Chemistry, 1985, vol. 50, # 8, p. 1239 - 1246
[12] Acta chemica Scandinavica. Series B: Organic chemistry and biochemistry, 1986, vol. 40, # 4, p. 242 - 249
[13] Chinese Chemical Letters, 2012, vol. 23, # 3, p. 297 - 300
[14] Bulletin of the Korean Chemical Society, 2012, vol. 33, # 8, p. 2777 - 2780
[15] Journal of Medicinal Chemistry, 2013, vol. 56, # 7, p. 2936 - 2947
[16] Journal of the American Chemical Society, 2014, vol. 136, # 26, p. 9244 - 9247
[17] Patent: CN106187819, 2016, A, . Location in patent: Paragraph 024; 0025; 0026; 0027
  • 42
  • [ 70-47-3 ]
  • [ 7536-55-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 10, p. 3103 - 3108
  • 43
  • [ 1070-19-5 ]
  • [ 70-47-3 ]
  • [ 7536-55-2 ]
Reference: [1] Synthesis, 1974, p. 661 - 662
[2] Justus Liebigs Annalen der Chemie, 1964, vol. 673, p. 208 - 220
  • 44
  • [ 70-47-3 ]
  • [ 18595-34-1 ]
  • [ 7536-55-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1968, vol. 716, p. 175 - 185
[2] Justus Liebigs Annalen der Chemie, 1971, vol. 743, p. 57 - 68
  • 45
  • [ 70-47-3 ]
  • [ 7536-55-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1969, vol. 725, p. 212 - 221
  • 46
  • [ 70-47-3 ]
  • [ 58632-95-4 ]
  • [ 7536-55-2 ]
Reference: [1] Tetrahedron Letters, 1975, p. 4393 - 4394
  • 47
  • [ 70-47-3 ]
  • [ 13303-10-1 ]
  • [ 7536-55-2 ]
Reference: [1] Helvetica Chimica Acta, 1963, vol. 46, p. 1637 - 1669
  • 48
  • [ 70-47-3 ]
  • [ 16965-08-5 ]
  • [ 7536-55-2 ]
Reference: [1] Journal of the Chemical Society [Section] C: Organic, 1967, p. 2632 - 2636
  • 49
  • [ 47091-50-9 ]
  • [ 70-47-3 ]
  • [ 5241-58-7 ]
Reference: [1] Chemistry - A European Journal, 2000, vol. 6, # 21, p. 3906 - 3913
  • 50
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  • [ 2304-96-3 ]
YieldReaction ConditionsOperation in experiment
84% With sodium carbonate In 1,4-dioxane at 0 - 20℃; Inert atmosphere To a solution of 6.05 g (0.45mmol) of L-asparagine in100 mL of 10percent Na2CO3 were added 56 mL of 1,4-dioxane and6.9 mL (0.04 mmol) of benzyl chloroformate at 0oC. The reactionmixture was stirred overnight at room temperature and was poured into 300 mL ofH2O. The mixture was washed three times with diethyl ether. Theaqueous layer was acidified with 2N HClin water and a white precipitate fell out. The precipitate was filtered off andwashed extensively with diethyl ether to afford compound 14 as off white solid(9 g, 84percent isolatedyield); MS (ESI): m/z=267 [M+H]+, 289 [M+Na]+.
75% With water; sodium hydrogencarbonate; sodium carbonate In acetone at 15 - 20℃; General procedure: The (S)-amino acid (10.0 g) was dissolved in H2O (300 ml) and Na2CO3 (2.0 equiv) and NaHCO3 (1.0 equiv) were added at rt, with stirring, to give a clear solution. Acetone (4.0 vol, with respect to the amino acid) was added and the slightly turbid solution was cooled in an ice water bath to 15-20 °C. Cbz-Cl (1.25 equiv) was added slowly, with stirring, and the reaction mixture allowed to warm to rt. After stirring for an additional 3 h at rt the mixture was extracted with Et2O (50 ml). To the aqueous phase was slowly added aqueous HCl to give a pH of 2. The resulting oil was extracted into EtOAc (150 ml) and this was washed with H2O (100 ml) and then concentrated in vacuo to give the N-Cbz amino acid as a white solid, see Table 1.
Reference: [1] Tetrahedron Asymmetry, 2015, vol. 26, # 21-22, p. 1273 - 1280
[2] Tetrahedron, 2000, vol. 56, # 16, p. 2513 - 2522
[3] Tetrahedron Letters, 2015, vol. 56, # 26, p. 3999 - 4001
[4] European Journal of Organic Chemistry, 2014, vol. 2014, # 31, p. 7015 - 7022
[5] Chemical Communications, 2016, vol. 52, # 60, p. 9438 - 9441
[6] Tetrahedron Letters, 2000, vol. 41, # 10, p. 1637 - 1641
[7] Chemistry - A European Journal, 2015, vol. 21, # 32, p. 11340 - 11343
[8] Tetrahedron Letters, 2011, vol. 52, # 13, p. 1493 - 1494
[9] Journal of the Chemical Society - Dalton Transactions, 1999, # 4, p. 599 - 606
[10] Tetrahedron, 1997, vol. 53, # 6, p. 2075 - 2086
[11] Chemische Berichte, 1932, vol. 65, p. 1192,1198
[12] Journal of medicinal chemistry, 1971, vol. 14, # 11, p. 1142 - 1143
[13] Journal of Organic Chemistry, 1961, vol. 26, p. 3356 - 3360
[14] Journal of Organic Chemistry, 1995, vol. 60, # 21, p. 6654 - 6655
[15] Chimia, 1996, vol. 50, # 11, p. 532 - 537
[16] Pharmaceutical Chemistry Journal, 1995, vol. 29, # 1, p. 14 - 17[17] Khimiko-Farmatsevticheskii Zhurnal, 1995, vol. 29, # 1, p. 15 - 18
[18] Tetrahedron Letters, 2003, vol. 44, # 28, p. 5251 - 5253
[19] Journal of Organic Chemistry, 2002, vol. 67, # 12, p. 4017 - 4029
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  • [ 70-47-3 ]
  • [ 2304-96-3 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 10, p. 3103 - 3108
  • 52
  • [ 70-47-3 ]
  • [ 2304-96-3 ]
Reference: [1] Helvetica Chimica Acta, 1955, vol. 38, p. 1491,1499
[2] Collection of Czechoslovak Chemical Communications, 1959, vol. 24, p. 1993,2002
  • 53
  • [ 76-84-6 ]
  • [ 70-47-3 ]
  • [ 132388-58-0 ]
Reference: [1] Tetrahedron Letters, 1991, vol. 32, # 6, p. 739 - 742
[2] Organic Letters, 2002, vol. 4, # 21, p. 3767 - 3769
[3] Patent: WO2004/7427, 2004, A1, . Location in patent: Page 51-52
  • 54
  • [ 70-47-3 ]
  • [ 82911-69-1 ]
  • [ 71989-16-7 ]
Reference: [1] Journal of Peptide Science, 2017, vol. 23, # 3, p. 202 - 214
[2] Synthetic Communications, 2009, vol. 39, # 11, p. 2022 - 2031
  • 55
  • [ 70-47-3 ]
  • [ 88744-04-1 ]
  • [ 71989-16-7 ]
Reference: [1] Synthesis, 1986, # 4, p. 303 - 305
  • 56
  • [ 70-47-3 ]
  • [ 28920-44-7 ]
  • [ 71989-16-7 ]
Reference: [1] Organic Process Research and Development, 2004, vol. 8, # 6, p. 920 - 924
  • 57
  • [ 70-47-3 ]
  • [ 28920-43-6 ]
  • [ 71989-16-7 ]
Reference: [1] Russian Journal of General Chemistry, 2010, vol. 80, # 12, p. 2572 - 2589
[2] Journal of the Chinese Chemical Society, 2011, vol. 58, # 4, p. 509 - 515
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