Home Cart 0 Sign in  

[ CAS No. 7536-55-2 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 7536-55-2
Chemical Structure| 7536-55-2
Structure of 7536-55-2 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 7536-55-2 ]

Related Doc. of [ 7536-55-2 ]

Alternatived Products of [ 7536-55-2 ]

Product Details of [ 7536-55-2 ]

CAS No. :7536-55-2 MDL No. :MFCD00038152
Formula : C9H16N2O5 Boiling Point : -
Linear Structure Formula :- InChI Key :FYYSQDHBALBGHX-YFKPBYRVSA-N
M.W :232.23 Pubchem ID :82035
Synonyms :

Calculated chemistry of [ 7536-55-2 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.67
Num. rotatable bonds : 7
Num. H-bond acceptors : 5.0
Num. H-bond donors : 3.0
Molar Refractivity : 54.57
TPSA : 118.72 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) : -8.14 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.99
Log Po/w (XLOGP3) : -0.59
Log Po/w (WLOGP) : -0.16
Log Po/w (MLOGP) : -0.48
Log Po/w (SILICOS-IT) : -0.91
Consensus Log Po/w : -0.23

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.45
Solubility : 83.1 mg/ml ; 0.358 mol/l
Class : Very soluble
Log S (Ali) : -1.43
Solubility : 8.59 mg/ml ; 0.037 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.26
Solubility : 129.0 mg/ml ; 0.555 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.86

Safety of [ 7536-55-2 ]

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 [ 7536-55-2 ]

* 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 [ 7536-55-2 ]
  • Downstream synthetic route of [ 7536-55-2 ]

[ 7536-55-2 ] Synthesis Path-Upstream   1~27

  • 1
  • [ 7536-55-2 ]
  • [ 70-47-3 ]
Reference: [1] Tetrahedron Letters, 2014, vol. 55, # 30, p. 4149 - 4151
  • 2
  • [ 70-47-3 ]
  • [ 24424-99-5 ]
  • [ 7536-55-2 ]
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
  • 3
  • [ 117334-80-2 ]
  • [ 7536-55-2 ]
Reference: [1] Organic Letters, 2005, vol. 7, # 9, p. 1723 - 1724
  • 4
  • [ 70-47-3 ]
  • [ 7536-55-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 10, p. 3103 - 3108
  • 5
  • [ 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
  • 6
  • [ 24424-99-5 ]
  • [ 7536-55-2 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1989, vol. 62, # 10, p. 3103 - 3108
  • 7
  • [ 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
  • 8
  • [ 98115-12-9 ]
  • [ 7536-55-2 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 1986, vol. 34, # 8, p. 3506 - 3509
  • 9
  • [ 70-47-3 ]
  • [ 7536-55-2 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1969, vol. 725, p. 212 - 221
  • 10
  • [ 70-47-3 ]
  • [ 58632-95-4 ]
  • [ 7536-55-2 ]
Reference: [1] Tetrahedron Letters, 1975, p. 4393 - 4394
  • 11
  • [ 70-47-3 ]
  • [ 13303-10-1 ]
  • [ 7536-55-2 ]
Reference: [1] Helvetica Chimica Acta, 1963, vol. 46, p. 1637 - 1669
  • 12
  • [ 4587-33-1 ]
  • [ 7536-55-2 ]
Reference: [1] Biopolymers, 2017, vol. 108, # 1,
  • 13
  • [ 4587-33-1 ]
  • [ 100-02-7 ]
  • [ 7536-55-2 ]
Reference: [1] Journal of the Chemical Society, Chemical Communications, 1986, # 8, p. 597 - 598
  • 14
  • [ 70-47-3 ]
  • [ 16965-08-5 ]
  • [ 7536-55-2 ]
Reference: [1] Journal of the Chemical Society [Section] C: Organic, 1967, p. 2632 - 2636
  • 15
  • [ 7536-55-2 ]
  • [ 100-39-0 ]
  • [ 13512-57-7 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 1998, vol. 6, # 8, p. 1185 - 1208
[2] Organic Letters, 2015, vol. 17, # 6, p. 1545 - 1548
[3] Organic Letters, 2015, vol. 17, # 9, p. 2294 - 2294
[4] Journal of Organic Chemistry, 1977, vol. 42, p. 1286 - 1290
[5] Journal of Organic Chemistry, 1985, vol. 50, # 8, p. 1239 - 1246
[6] Organic and Biomolecular Chemistry, 2008, vol. 6, # 10, p. 1849 - 1852
[7] Journal of the American Chemical Society, 2014, vol. 136, # 26, p. 9244 - 9247
  • 16
  • [ 7536-55-2 ]
  • [ 100-51-6 ]
  • [ 13512-57-7 ]
  • [ 95407-39-9 ]
YieldReaction ConditionsOperation in experiment
90 %Chromat. With dmap; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride In dichloromethane at 0 - 20℃; for 12 h; Inert atmosphere General procedure: To a stirred solution of N-protected-L-asparagin 1a-c (0.10 mmol) and alcohol or amine 2a-n (0.12 mmol) inDCM (5 mL), EDC.HCl (0.30 mmol) and DMAP (0.02 mmol) were added at 0 oC. This reaction mixture was stirred for 12h at room temperature. Then the reaction mixture was poured in H2O (10 mL) and extracted with DCM (20 mL). The organic phase was separated, dried, and subjected to flash column chromatography (EtOAc–hexane, 1: 4) to afford the desired compounds as white solids.
Reference: [1] Synlett, 2016, vol. 27, # 2, p. 309 - 312
  • 17
  • [ 7536-55-2 ]
  • [ 13512-57-7 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1996, vol. 69, # 4, p. 1099 - 1106
  • 18
  • [ 7536-55-2 ]
  • [ 13512-57-7 ]
Reference: [1] Patent: US4148788, 1979, A,
[2] Patent: US4116951, 1978, A,
  • 19
  • [ 7536-55-2 ]
  • [ 13512-57-7 ]
Reference: [1] Patent: US6528655, 2003, B1,
  • 20
  • [ 7536-55-2 ]
  • [ 41088-86-2 ]
Reference: [1] Journal of Organic Chemistry, 1983, vol. 48, # 11, p. 1916 - 1919
[2] Journal of the Chemical Society, Chemical Communications, 1982, # 11, p. 639 - 640
  • 21
  • [ 7536-55-2 ]
  • [ 65710-57-8 ]
Reference: [1] Synthesis, 1981, vol. No.4, p. 266 - 268
[2] Chemical Communications, 2011, vol. 47, # 4, p. 1198 - 1200
[3] Journal of Organic Chemistry, 2012, vol. 77, # 13, p. 5696 - 5704
[4] Organic and Biomolecular Chemistry, 2015, vol. 13, # 6, p. 1629 - 1633
[5] Organic and Biomolecular Chemistry, 2015, vol. 13, # 15, p. 4570 - 4580
  • 22
  • [ 7536-55-2 ]
  • [ 501-53-1 ]
  • [ 65710-57-8 ]
Reference: [1] Tetrahedron Letters, 1992, vol. 33, # 30, p. 4275 - 4278
  • 23
  • [ 7536-55-2 ]
  • [ 76387-70-7 ]
YieldReaction ConditionsOperation in experiment
66% With [bis(acetoxy)iodo]benzene In water; ethyl acetate; acetonitrile at 16 - 20℃; for 4.5 h; N-Boc-L-asparagine (13; 3.48 g, 15 mmol) and PIDA (5.81 g, 18 mmol)were dissolved in a mixture of EtOAc, MeCN, and H2O (2:2:1, 62.5 mL)and stirred at 16 °C for 30 min. Afterwards, the reaction mixture wasallowed to warm up to r.t. and stirred for 4 h whereupon a precipitatewas formed, which was collected by filtration and dried; yield: 2.02 g(66percent, 9.89 mmol); colorless solid; mp 211–213 °C (Lit.25 mp 216 °C).1H NMR (500 MHz, DMSO-d6): δ = 1.40 [s, 9 H, C(CH3)3], 2.76 (dd,3J = 9.2 Hz, 2J = 11.8 Hz, 1 H, CH2), 3.06 (dd, 3J = 5.1 Hz, 2J = 11.8 Hz, 1H, CH2), 3.65–3.69 (m, 1 H, COCH), 6.08 (s, 1 H, OCONH). Protons ofCO2H and the NH2 group were not detected.13C NMR (125 MHz, DMSO-d6): δ = 28.3, 40.8, 51.1, 78.2, 155.2, 171.2.LC-MS (ESI): 100percent purity; m/z = 205.19 ([M + H]+), 203.09 ([M – H]–).HRMS (ESI+): m/z calcd for C8H16N2O4 ([M + H]+): 205.1183; found:205.1177.
57% With [bis(acetoxy)iodo]benzene In water; ethyl acetate; acetonitrile at 5 - 25℃; for 3 - 4 h; N-tert-butoxycarbonyl-L-asparagine, from step 1 of Example G. 5 or commercially available, (8 g, 0.034 mol, leq. ) was suspended in ethyl acetate (72 ml), acetonitrile (72ml) and water (36ml), and IODOBENZENEDIACETATE (13,3 g, 0. 041 mol, 1,2 eq. ) was added at 5°C. The mixture was stirred at 10°-25°C for 3-4h, then a white solid came off.. The solid was filtered, washed with diethyl ether and dried under vacuum to give a white powder. Yield 57percent. 4g. Analytical data: m. p. 210°C-211°C. Silica gel (dicloromethane/methanol/acetic acid 5/3/1) RF 0, 5. H NMR (DMSO-d6) 4.15 (1H, t); 3.15 (2H, M) ; 1.45 (9H, s);
57% With [bis(acetoxy)iodo]benzene In water; ethyl acetate; acetonitrile at 5 - 25℃; for 3 - 4 h; N-tert-butoxycarbonyl-L-asparagine, from step 1 of Example G.5 or commercially available, (8 g, 0.034 mol. 1 eq.) was suspended in ethyl acetate (72 ml), acetonitrile (72 ml) and water (36 ml), and iodobenzenediacetate (13.3 g, 0.041 mol. 1.2 eq.) was added at 5° C.
The mixture was stirred at 10°-25° C. for 3-4 h, then a white solid came off.
The solid was filtered, washed with diethyl ether and dried under vacuum to give a white powder.
Yield 57percent.4 g.
Analytical data: m.p. 210° C.-211° C. Silica gel (dicloromethane/methanol/acetic acid 5/3/1) Rf 0.5. 1H NMR (DMSO-d6) 4.15 (1H, t); 3.15 (2H, m); 1.45 (9H, s);
Reference: [1] Organic and Biomolecular Chemistry, 2015, vol. 13, # 6, p. 1629 - 1633
[2] Chemical Communications, 2011, vol. 47, # 4, p. 1198 - 1200
[3] Journal of Organic Chemistry, 2012, vol. 77, # 13, p. 5696 - 5704
[4] Synlett, 2008, # 4, p. 513 - 516
[5] Journal of Peptide Science, 2017, vol. 23, # 3, p. 202 - 214
[6] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 1, p. 161 - 175
[7] Organic Letters, 2007, vol. 9, # 1, p. 25 - 28
[8] Bioorganic and Medicinal Chemistry Letters, 2006, vol. 16, # 23, p. 6039 - 6042
[9] Journal of Medicinal Chemistry, 2009, vol. 52, # 15, p. 4650 - 4656
[10] Organic and Biomolecular Chemistry, 2015, vol. 13, # 15, p. 4570 - 4580
[11] Synthesis (Germany), 2016, vol. 48, # 2, p. 245 - 255
[12] Journal of Organic Chemistry, 2014, vol. 79, # 14, p. 6708 - 6714
[13] Journal of Organic Chemistry, 2014, vol. 79, # 4, p. 1542 - 1554
[14] Journal of Organic Chemistry, 1997, vol. 62, # 20, p. 6918 - 6920
[15] Journal of Medicinal Chemistry, 2008, vol. 51, # 15, p. 4581 - 4588
[16] Synthesis, 1981, vol. No.4, p. 266 - 268
[17] Angewandte Chemie - International Edition, 2007, vol. 46, # 14, p. 2470 - 2477
[18] Patent: WO2005/21558, 2005, A2, . Location in patent: Page/Page column 223-224
[19] Patent: US2006/189806, 2006, A1, . Location in patent: Page/Page column 44
[20] Organic Letters, 2004, vol. 6, # 2, p. 213 - 215
[21] Bulletin of the Chemical Society of Japan, 1992, vol. 65, # 8, p. 2227 - 2240
[22] Journal of the Chemical Society, Chemical Communications, 1993, # 23, p. 1786 - 1788
[23] Tetrahedron, 1994, vol. 50, # 33, p. 9873 - 9882
[24] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 6, p. 997 - 1000
[25] Chemical and Pharmaceutical Bulletin, 2005, vol. 53, # 9, p. 1152 - 1158
  • 24
  • [ 7536-55-2 ]
  • [ 25691-37-6 ]
Reference: [1] Journal of Organic Chemistry, 1991, vol. 56, # 14, p. 4347 - 4354
  • 25
  • [ 7536-55-2 ]
  • [ 73259-81-1 ]
Reference: [1] Organic and Biomolecular Chemistry, 2013, vol. 11, # 5, p. 773 - 780
[2] Tetrahedron, 1994, vol. 50, # 33, p. 9873 - 9882
[3] Tetrahedron Letters, 1998, vol. 39, # 49, p. 8925 - 8928
[4] Bioorganic and Medicinal Chemistry Letters, 2003, vol. 13, # 13, p. 2101 - 2104
[5] Chemical Communications, 2011, vol. 47, # 4, p. 1198 - 1200
[6] Journal of Organic Chemistry, 2012, vol. 77, # 13, p. 5696 - 5704
  • 26
  • [ 64-17-5 ]
  • [ 7536-55-2 ]
  • [ 84787-81-5 ]
Reference: [1] Tetrahedron, 1987, vol. 43, # 8, p. 1823 - 1826
  • 27
  • [ 7536-55-2 ]
  • [ 721927-81-7 ]
Reference: [1] Chemical Communications, 2011, vol. 47, # 4, p. 1198 - 1200
[2] Journal of Organic Chemistry, 2012, vol. 77, # 13, p. 5696 - 5704
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 7536-55-2 ]

Amino Acid Derivatives

Chemical Structure| 61348-28-5

[ 61348-28-5 ]

Boc-D-Gln-OH

Similarity: 0.95

Chemical Structure| 13726-85-7

[ 13726-85-7 ]

Boc-Gln-OH

Similarity: 0.95

Chemical Structure| 80445-78-9

[ 80445-78-9 ]

Boc-D-Dab-OH

Similarity: 0.95

Chemical Structure| 25691-37-6

[ 25691-37-6 ]

Boc-Dab-OH

Similarity: 0.95

Chemical Structure| 84787-81-5

[ 84787-81-5 ]

(S)-Ethyl 4-amino-2-((tert-butoxycarbonyl)amino)-4-oxobutanoate

Similarity: 0.93