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[ CAS No. 31972-52-8 ] {[proInfo.proName]}

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Chemical Structure| 31972-52-8
Chemical Structure| 31972-52-8
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Product Details of [ 31972-52-8 ]

CAS No. :31972-52-8 MDL No. :MFCD00038558
Formula : C9H16N2O5 Boiling Point : -
Linear Structure Formula :- InChI Key :HWBAHOVOSOAFLE-UHFFFAOYSA-N
M.W : 232.23 Pubchem ID :333466
Synonyms :

Calculated chemistry of [ 31972-52-8 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.67
Num. rotatable bonds : 8
Num. H-bond acceptors : 5.0
Num. H-bond donors : 3.0
Molar Refractivity : 54.66
TPSA : 104.73 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) : -7.81 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.31
Log Po/w (XLOGP3) : -0.13
Log Po/w (WLOGP) : -0.29
Log Po/w (MLOGP) : -0.48
Log Po/w (SILICOS-IT) : -0.67
Consensus Log Po/w : -0.05

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.67
Solubility : 49.7 mg/ml ; 0.214 mol/l
Class : Very soluble
Log S (Ali) : -1.62
Solubility : 5.63 mg/ml ; 0.0242 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -1.02
Solubility : 22.0 mg/ml ; 0.0948 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 2.26

Safety of [ 31972-52-8 ]

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 [ 31972-52-8 ]

* 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 [ 31972-52-8 ]
  • Downstream synthetic route of [ 31972-52-8 ]

[ 31972-52-8 ] Synthesis Path-Upstream   1~17

  • 1
  • [ 31972-52-8 ]
  • [ 28320-73-2 ]
Reference: [1] Australian Journal of Chemistry, 1987, vol. 40, # 1, p. 97 - 105
  • 2
  • [ 556-50-3 ]
  • [ 24424-99-5 ]
  • [ 31972-52-8 ]
YieldReaction ConditionsOperation in experiment
96% With guanidine hydrochloride In ethanol at 35 - 40℃; for 9 h; General procedure: Amino acid or peptide (1 mmol) was added with stirring to a solution of guanidine hydrochloride (15 molpercent) and di-tert-butyl dicarbonate (2.5-3 mmol) in EtOH (1 mL), at 35-40°C. The reaction mixture was continued to stir until a clear solution was obtained. EtOH was evaporated under vacuum and the residue was successively washed with water (2 mL) and hexane or petroleum ether (2 mL) to afford almost pure N-Boc amino acids or N-Boc peptides. If necessary, the crude products could be recrystallized for further purification.
88% With triethylamine In 1,4-dioxane; water at 23℃; for 16 h; Et3N (3.16 mL, 22.71 mmol) and Boc2O (3.63 g, 16.65 mmol) wereadded to a suspension of diglycine (7; 2.00 g, 15.14 mmol) in a mixtureof dioxane (60 mL) and H2O (10 mL) at 0 °C. The mixture wasstirred at 23 °C for 16 h, diluted with H2O (250 mL), and acidifiedto pH 3 by addition of solid KHSO4. The mixture was extracted withEtOAc (5 × 50 mL), the combined organic phases were dried(Na2SO4), and all solvents were removed under reduced pressure;this gave 8 as a white solid, which was used without further purification.Yield: 3.10 g (13.35 mmol, 88percent).1H NMR (400 MHz, DMSO): δ = 12.55 (br s, 1 H), 8.03 (t, J = 5.5Hz, 1 H), 6.96 (t, J = 5.7 Hz, 1 H), 3.75 (d, J = 5.7 Hz, 2 H), 3.56 (d,J = 5.8 Hz, 2 H), 1.37 (s, 9 H).
88% With triethylamine In 1,4-dioxane; water at 23℃; for 16 h; Triethylamine (Et3N)(3.16 mL, 22.71 mmol) and Boc2O (3.63 g, 16.65 mmol)were added to a suspension of diglycine (2.00 g,15.14 mmol) in a mixture of dioxane (60 mL) and H2O(10 mL) at 0 C. The reaction mixture was maintained withstirring at 23 C for 16 h. Then, H2O (250 mL) was added,and the reaction mixture was acidified to pH 3 by the additionof solid KHSO4. The product was extracted with ethylacetate (5 × 50 mL), and residual water in the organicphases was removed with Na2SO4. Finally, all solventswere removed using a rotary evaporator to yield product6 as a white solid without purification. Yield: 3.10 g (88percent).1H NMR (300 MHz, DMSO‑d6) 12.6 (s, 1H), 8.0 (t, 1H,J = 5.8 Hz), 7.0 (t, 1H, J = 6.0 Hz), 3.8 (d, 2H,J = 5.8 Hz), 3.7 (d, 2H, J = 6.1 Hz), 1.4 (s, 9H). 13C NMR(125 MHz, DMSO‑d6) 174.6, 171.0, 156.2, 79.5, 44.6,42.6, 28.4. ESI-MS (m/z) calcd. For C9H16N2O5: 232.1;233.004 [M + H]+. Elemental analysis: calculated forC9H16N2O5: C 46.6, H 6.9, N 12.1. Found: C 46.5, H 7.3,N 12.1.
Reference: [1] Tetrahedron Letters, 2011, vol. 52, # 12, p. 1260 - 1264
[2] European Journal of Inorganic Chemistry, 2016, vol. 2016, # 35, p. 5427 - 5434
[3] Synthesis (Germany), 2013, vol. 45, # 17, p. 2426 - 2430
[4] Bulletin of the Korean Chemical Society, 2018, vol. 39, # 8, p. 988 - 994
[5] Journal of Polymer Science, Part A: Polymer Chemistry, 2018, vol. 56, # 8, p. 914 - 921
[6] Organic and Biomolecular Chemistry, 2006, vol. 4, # 19, p. 3626 - 3638
[7] Chemical Communications, 2015, vol. 51, # 77, p. 14501 - 14504
[8] Journal of Medicinal Chemistry, 2016, vol. 59, # 7, p. 3331 - 3339
[9] Chemistry - A European Journal, 2007, vol. 13, # 8, p. 2358 - 2368
[10] Angewandte Chemie - International Edition, 2013, vol. 52, # 32, p. 8411 - 8415[11] Angew. Chem., 2013, vol. 125, # 32, p. 8569 - 8573
[12] Inorganica Chimica Acta, 2016, vol. 450, p. 211 - 215
[13] Analytical Biochemistry, 2016, vol. 512, p. 114 - 119
[14] Tetrahedron, 2017, vol. 73, # 22, p. 3173 - 3180
  • 3
  • [ 31972-51-7 ]
  • [ 31972-52-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2008, vol. 18, # 20, p. 5512 - 5517
[2] Bulletin of the Chemical Society of Japan, 1983, vol. 56, # 6, p. 1678 - 1681
[3] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 12, p. 4448 - 4456
[4] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, p. 803 - 808
[5] Journal of Medicinal Chemistry, 1980, vol. 23, # 10, p. 1113 - 1122
[6] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1985, p. 535 - 540
[7] Bulletin of the Chemical Society of Japan, 1986, vol. 59, p. 3553 - 3558
[8] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 23, p. 8365 - 8373
[9] Molecular Pharmaceutics, 2011, vol. 8, # 4, p. 1224 - 1232
[10] International Journal of Pharmaceutics, 2014, vol. 468, # 1-2, p. 133 - 141
  • 4
  • [ 53487-98-2 ]
  • [ 31972-52-8 ]
Reference: [1] Organic Letters, 2015, vol. 17, # 16, p. 4106 - 4109
[2] Chemistry - A European Journal, 2008, vol. 14, # 29, p. 8922 - 8927
[3] European Journal of Medicinal Chemistry, 1999, vol. 34, # 6, p. 525 - 529
[4] Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences, 2005, vol. 60, # 12, p. 1313 - 1320
[5] Polymer, 2012, vol. 53, # 8, p. 1694 - 1702
[6] Chemistry - An Asian Journal, 2018, vol. 13, # 4, p. 400 - 403
[7] Beilstein Journal of Organic Chemistry, 2018, vol. 14, p. 1112 - 1119
[8] Patent: US4169141, 1979, A,
  • 5
  • [ 25438-03-3 ]
  • [ 31972-52-8 ]
Reference: [1] Tetrahedron Letters, 1976, p. 2119 - 2120
[2] Patent: CN106749223, 2017, A, . Location in patent: Paragraph 0222; 0223; 0224
  • 6
  • [ 4530-20-5 ]
  • [ 31972-52-8 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1986, vol. 59, p. 3553 - 3558
[2] Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 8, p. 2433 - 2438
[3] Journal of the Chemical Society, Dalton Transactions: Inorganic Chemistry (1972-1999), 1985, p. 535 - 540
[4] Journal of Medicinal Chemistry, 1980, vol. 23, # 10, p. 1113 - 1122
[5] Chemical and Pharmaceutical Bulletin, 1982, vol. 30, # 12, p. 4448 - 4456
[6] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1983, p. 803 - 808
[7] Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 11B, p. 2787 - 2790
[8] Collection of Czechoslovak Chemical Communications, 1990, vol. 55, # 9, p. 2357 - 2359
[9] Tetrahedron Letters, 1976, p. 2119 - 2120
[10] Molecular Pharmaceutics, 2011, vol. 8, # 4, p. 1224 - 1232
[11] Polymer, 2012, vol. 53, # 8, p. 1694 - 1702
[12] Science China Chemistry, 2013, vol. 56, # 2, p. 159 - 168
[13] International Journal of Pharmaceutics, 2014, vol. 468, # 1-2, p. 133 - 141
[14] Organic Letters, 2015, vol. 17, # 16, p. 4106 - 4109
[15] Chemical Biology and Drug Design, 2016, vol. 88, # 6, p. 884 - 888
[16] Patent: CN106749223, 2017, A,
[17] Chemistry - An Asian Journal, 2018, vol. 13, # 4, p. 400 - 403
[18] Beilstein Journal of Organic Chemistry, 2018, vol. 14, p. 1112 - 1119
  • 7
  • [ 3655-05-8 ]
  • [ 56-40-6 ]
  • [ 31972-52-8 ]
Reference: [1] Organic Process Research and Development, 2015, vol. 19, # 9, p. 1257 - 1262
  • 8
  • [ 236424-82-1 ]
  • [ 31972-52-8 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 1999, vol. 7, # 5, p. 749 - 762
  • 9
  • [ 24424-99-5 ]
  • [ 31972-52-8 ]
Reference: [1] Science China Chemistry, 2013, vol. 56, # 2, p. 159 - 168
[2] Organic Process Research and Development, 2015, vol. 19, # 9, p. 1257 - 1262
[3] Chemical Biology and Drug Design, 2016, vol. 88, # 6, p. 884 - 888
[4] Chemistry - An Asian Journal, 2018, vol. 13, # 4, p. 400 - 403
  • 10
  • [ 123872-97-9 ]
  • [ 31972-52-8 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1988, vol. 53, # 11B, p. 2787 - 2790
  • 11
  • [ 131326-18-6 ]
  • [ 31972-52-8 ]
Reference: [1] Collection of Czechoslovak Chemical Communications, 1990, vol. 55, # 9, p. 2357 - 2359
  • 12
  • [ 103339-87-3 ]
  • [ 31972-52-8 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 8, p. 2433 - 2438
  • 13
  • [ 83316-95-4 ]
  • [ 31972-52-8 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1986, vol. 59, # 8, p. 2433 - 2438
  • 14
  • [ 56-40-6 ]
  • [ 18185-77-8 ]
  • [ 31972-52-8 ]
Reference: [1] Science China Chemistry, 2013, vol. 56, # 2, p. 159 - 168
  • 15
  • [ 556-50-3 ]
  • [ 57022-34-1 ]
  • [ 31972-52-8 ]
Reference: [1] Bulletin de l'Academie Polonaise des Sciences, Serie des Sciences Chimiques, 1964, vol. 12, p. 21 - 24
  • 16
  • [ 66866-43-1 ]
  • [ 56-40-6 ]
  • [ 31972-52-8 ]
Reference: [1] Chemical Biology and Drug Design, 2016, vol. 88, # 6, p. 884 - 888
  • 17
  • [ 6066-82-6 ]
  • [ 31972-52-8 ]
  • [ 29248-48-4 ]
YieldReaction ConditionsOperation in experiment
65.4 mg
Stage #1: With 2,4,6-tripropyl-1,3,5,2,4,6-trioxatriphosphinane-2,4,6-trioxide; triethylamine In dichloromethane at 20℃; for 0.333333 h;
Stage #2: for 48 h;
To a solution of Gly-Gly (1.00 g, 7.57 mmol) in dioxane:water (30:5 mL) at room temperature was added triethylamine (1.15 g,11.4 mmol) and di-tert-butyl-dicarbonate (1.84 g, 8.33 mmol) consecutively. The mixture was stirred at room temperature overnight, then diluted with water, acidified to approximately pH 2via the addition of solid KHSO4, extracted with EtOAc, dried(Na2SO4), and concentrated in vacuo to afford (tert-butoxycarbonyl)glycylglycine [8] as a white solid. To a solution of crude (tertbutoxycarbonyl)glycylglycine (0.106 g, 0.451 mmol) in anhydrous dichloromethane (5.00 mL) was added triethylamine (45.6 mg,0.451 mmol) and propylphosphonic anhydride solution (T3P®) [9] (0.344 g, 0.541 mmol) at room temperature. The mixture was stirred for 20 min, followed by the addition of N-hydroxy succinimide (51.9 mg, 0.451 mmol). The reaction was stirred for 48 h and upon completion, the organic layer was washed with brine (3),dried (Na2SO4), and concentrated in vacuo to afford the product as a white solid. The crude solid was triturated from diethyl ether toafford 65.4 mg (44percent) of the product as a white solid: 1H NMR(400 MHz, CDCl3) d 6.76 (brs, 1 H), 5.15 (brs, 1 H), 4.43 (d, 2 H,J 5.7 Hz), 3.87 (d, 2 H, J 5.3 Hz), 2.85 (s, 4 H), 1.45 (s, 9 H); ESIMSm/z 330 [MH]. Direct infusion ESI-MS on a high resolution accurate mass measurements (Exactive Plus, Thermo Fisher Scientific) in the negative ion mode yielded an elemental composition of the expected product within 5 ppm (see Fig. 1).
Reference: [1] Bioorganic and Medicinal Chemistry, 2004, vol. 12, # 22, p. 5973 - 5982
[2] Journal of Pharmaceutical Sciences, 1984, vol. 73, # 2, p. 275 - 277
[3] Analytical Biochemistry, 2016, vol. 512, p. 114 - 119
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