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[ CAS No. 2212-75-1 ] {[proInfo.proName]}

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Chemical Structure| 2212-75-1
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Product Details of [ 2212-75-1 ]

CAS No. :2212-75-1 MDL No. :MFCD00038204
Formula : C14H20N2O4 Boiling Point : -
Linear Structure Formula :C6H14N2O2C8H6O2 InChI Key :OJTJKAUNOLVMDX-LBPRGKRZSA-N
M.W : 280.32 Pubchem ID :75172
Synonyms :
Z-Lys-OH;Nα-(Benzyloxycarbonyl)lysine;α-Carbobenzoxy-L-lysine
Chemical Name :(S)-6-Amino-2-(((benzyloxy)carbonyl)amino)hexanoic acid

Calculated chemistry of [ 2212-75-1 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.43
Num. rotatable bonds : 10
Num. H-bond acceptors : 5.0
Num. H-bond donors : 3.0
Molar Refractivity : 74.01
TPSA : 101.65 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) : -8.78 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.52
Log Po/w (XLOGP3) : -1.08
Log Po/w (WLOGP) : 1.34
Log Po/w (MLOGP) : 1.15
Log Po/w (SILICOS-IT) : 1.14
Consensus Log Po/w : 0.81

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.46
Solubility : 97.3 mg/ml ; 0.347 mol/l
Class : Very soluble
Log S (Ali) : -0.57
Solubility : 76.3 mg/ml ; 0.272 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.22
Solubility : 0.168 mg/ml ; 0.000598 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.89

Safety of [ 2212-75-1 ]

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 [ 2212-75-1 ]

* 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 [ 2212-75-1 ]
  • Downstream synthetic route of [ 2212-75-1 ]

[ 2212-75-1 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 56-87-1 ]
  • [ 501-53-1 ]
  • [ 2212-75-1 ]
Reference: [1] Patent: CN103980341, 2016, B, . Location in patent: Paragraph 0105
  • 2
  • [ 14511-39-8 ]
  • [ 501-53-1 ]
  • [ 2212-75-1 ]
Reference: [1] Journal of the American Chemical Society, 1961, vol. 83, p. 719 - 722
[2] The Journal of organic chemistry, 1968, vol. 33, # 3, p. 1261 - 1264
[3] Chemische Berichte, 1964, vol. 97, p. 3305 - 3311
[4] Tetrahedron, 1988, vol. 44, # 9, p. 2633 - 2636
[5] Synthetic Communications, 1981, vol. 11, # 4, p. 303 - 314
[6] Organic Letters, 2004, vol. 6, # 21, p. 3781 - 3784
[7] Bioconjugate Chemistry, 2013, vol. 24, # 1, p. 26 - 35
  • 3
  • [ 2389-60-8 ]
  • [ 2212-75-1 ]
Reference: [1] Journal of the American Chemical Society, 1982, vol. 104, # 16, p. 4446 - 4450
[2] Patent: EP1426366, 2004, A1, . Location in patent: Page 28-29
  • 4
  • [ 657-27-2 ]
  • [ 2212-75-1 ]
Reference: [1] Organic Letters, 2004, vol. 6, # 21, p. 3781 - 3784
[2] Synthetic Communications, 2002, vol. 32, # 13, p. 2075 - 2082
[3] Synthetic Communications, 1981, vol. 11, # 4, p. 303 - 314
[4] Tetrahedron, 1988, vol. 44, # 9, p. 2633 - 2636
[5] Journal of the American Chemical Society, 1961, vol. 83, p. 719 - 722
  • 5
  • [ 1413890-77-3 ]
  • [ 2212-75-1 ]
Reference: [1] Journal of the American Chemical Society, 2012, vol. 134, # 47, p. 19463 - 19467
  • 6
  • [ 69861-90-1 ]
  • [ 2212-75-1 ]
  • [ 100-53-8 ]
Reference: [1] Journal of the American Chemical Society, 1990, vol. 112, # 3, p. 945 - 953
[2] Journal of the American Chemical Society, 1990, vol. 112, # 3, p. 945 - 953
[3] Bioscience, biotechnology, and biochemistry, 2001, vol. 65, # 4, p. 781 - 786
  • 7
  • [ 2418-95-3 ]
  • [ 2212-75-1 ]
Reference: [1] Journal of the American Chemical Society, 1982, vol. 104, # 16, p. 4446 - 4450
  • 8
  • [ 14511-39-8 ]
  • [ 2212-75-1 ]
Reference: [1] Synthetic Communications, 2002, vol. 32, # 13, p. 2075 - 2082
  • 9
  • [ 657-27-2 ]
  • [ 501-53-1 ]
  • [ 2212-75-1 ]
Reference: [1] Organic Preparations and Procedures International, 1999, vol. 31, # 4, p. 456 - 459
  • 10
  • [ 56-87-1 ]
  • [ 2212-75-1 ]
Reference: [1] Bioconjugate Chemistry, 2013, vol. 24, # 1, p. 26 - 35
  • 11
  • [ 47594-83-2 ]
  • [ 2212-75-1 ]
Reference: [1] Tetrahedron Letters, 1982, vol. 23, # 2, p. 249 - 252
[2] Tetrahedron Letters, 1982, vol. 23, # 2, p. 249 - 252
  • 12
  • [ 4272-71-3 ]
  • [ 100-02-7 ]
  • [ 2212-75-1 ]
Reference: [1] Gazzetta Chimica Italiana, 1982, vol. 112, # 7/8, p. 307 - 318
  • 13
  • [ 24424-99-5 ]
  • [ 2212-75-1 ]
  • [ 2389-60-8 ]
YieldReaction ConditionsOperation in experiment
100% With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; N-α-Cbz-(S)-Lysine (5g, 17.85mmol) was dissolved in a mixture of THF (5OmL) and water (5OmL). To this sodium bicarbonate (3g, 35.5mmol, 2eq) and a solution OfBoC2O (9g, 41mmol, 2.3eq) in THF (5OmL). After stirring at room temperature overnight, the THF was removed under reduced pressure and the resulting aqueous solution was neutralized with 2N HCl. This was extracted with ethyl acetate and the combined organic layers were washed with brine. The organic layer was dried with sodium sulfate and concentrated to a clear oil. Removal of excess BoC2O by Kugelrhor distillation resulted in a thick clear oil weighing 6.Sg, 100percent. 1HNMR (CDCl3) δ 11.6 (s, IH), 7.32 (s, 5H)5 6.36 (s, IH)5 5.75 (d, IH5 J=8)5 5.09 (s, 2H)5 4.37(m5 IH), 3.06 (m, 2H), 1.78 (m, 2H)5 1.53 (s, 4H)5 1.42 (s, 9H). 13C NMR (CDCl3) δ 174.8, 155.4, 135.4, 127.6, 127.3, 127.2, 78.6, 66.1, 52.9, 39.2, 31.0, 28.6, 27.5, 26.6, 21.4
100%
Stage #1: With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃;
Stage #2: With hydrogenchloride In water
a. Synthesis of Compound 1 (NBoc-Cbz Lysine) N-?-Cbz-(S)-Lysine (5 g, 17.85 mmol) was dissolved in a mixture of THF (50 mL) and water (50 mL). To this sodium bicarbonate (3 g, 35.5 mmol, 2 eq) and a solution of Boc2O (9 g, 41 mmol, 2.3 eq) in THF (50 mL). After stirring at room temperature overnight, the THF was removed under reduced pressure and the resulting aqueous solution was neutralized with 2N HCl. This was extracted with ethyl acetate and the combined organic layers were washed with brine. The organic layer was dried with sodium sulfate and concentrated to a clear oil. Removal of excess Boc2O by Kugelrhor distillation resulted in a thick clear oil weighing 6.8 g, 100percent. 1H NMR (CDCl3) ? 11.6 (s, 1H), 7.32 (s, 5H), 6.36 (s, 1H), 5.75 (d, 1H, J=8), 5.09 (s, 2H), 4.37 (m, 1H), 3.06 (m, 2H), 1.78 (m, 2H), 1.53 (s, 4H), 1.42 (s, 9H). 13C NMR (CDCl3) ? 174.8, 155.4, 135.4, 127.6, 127.3, 127.2, 78.6, 66.1, 52.9, 39.2, 31.0, 28.6, 27.5, 26.6, 21.4
100%
Stage #1: With sodium hydrogencarbonate In tetrahydrofuran at 20℃;
Example 6. Synthesis of Lysine Teroxazole Intermediate 309; A lysine teroxazole intermediate that can be used to prepare compounds of the invention can be prepared as follows <n="50"/>a. Synthesis of Compound 301 (NBoc-Cbz Lysine)N-α-Cbz-(S)-Lysine (5g, 17.85mmol) was dissolved in a mixture of THF (5OmL) and water (5OmL). To this sodium bicarbonate (3g, 35.5mmol, 2eq) and a solution of BoC2O (9g, 41mmol, 2.3eq) in THF (5OmL). After stirring at room temperature overnight, the THF was removed under reduced pressure and the resulting aqueous solution was neutralized with 2N HCl. This was extracted with ethyl acetate and the combined organic layers were washed with brine. The organic layer was dried with sodium sulfate and concentrated to a clear oil. Removal of excess BoC2O by Kugelrhor distillation resulted in a thick clear oil weighing 6.8g, 100percent. H NMR (CDCl3) δ 11.6 (s, IH), 7.32 (s, 5H), 6.36 (s, IH), 5.75 (d, IH, J=8), 5.09 (s, 2H), 4.37(m, IH), 3.06 (m, 2H), 1.78 (m, 2H), 1.53 (s, 4H), 1.42 (s, 9H). 13C NMR (CDCl3) δ 174.8, 155.4, 135.4, 127.6, 127.3, 127.2, 78.6, 66.1, 52.9, 39.2, 31.0, 28.6, 27.5, 26.6, 21.4.
Reference: [1] Patent: WO2007/127173, 2007, A2, . Location in patent: Page/Page column 34
[2] Patent: US2009/156627, 2009, A1, . Location in patent: Page/Page column 25
[3] Patent: WO2009/18549, 2009, A1, . Location in patent: Page/Page column 49
[4] Bioorganic and Medicinal Chemistry Letters, 2007, vol. 17, # 2, p. 305 - 308
[5] Journal of the Chemical Society - Perkin Transactions 1, 1998, # 2, p. 359 - 365
[6] Bioorganic and Medicinal Chemistry Letters, 2010, vol. 20, # 10, p. 3150 - 3154
  • 14
  • [ 1070-19-5 ]
  • [ 2212-75-1 ]
  • [ 2389-60-8 ]
Reference: [1] Journal of the American Chemical Society, 1965, vol. 87, p. 99 - 104
[2] Journal of the American Chemical Society, 1968, vol. 90, # 20, p. 5598 - 5603
[3] Journal of Organic Chemistry, 1971, vol. 36, p. 3022 - 3026
[4] Chemische Berichte, 1964, vol. 97, p. 3305 - 3311
[5] Justus Liebigs Annalen der Chemie, 1964, vol. 674, p. 218 - 225
  • 15
  • [ 2212-75-1 ]
  • [ 6627-89-0 ]
  • [ 2389-60-8 ]
Reference: [1] Synthetic Communications, 1981, vol. 11, # 4, p. 303 - 314
  • 16
  • [ 18595-34-1 ]
  • [ 2212-75-1 ]
  • [ 2389-60-8 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1968, vol. 716, p. 175 - 185
  • 17
  • [ 16965-08-5 ]
  • [ 2212-75-1 ]
  • [ 2389-60-8 ]
Reference: [1] Journal of the Chemical Society [Section] C: Organic, 1967, p. 2632 - 2636
  • 18
  • [ 2212-75-1 ]
  • [ 2418-95-3 ]
Reference: [1] Synthetic Communications, 1981, vol. 11, # 4, p. 303 - 314
[2] Journal of the American Chemical Society, 1965, vol. 87, p. 99 - 104
  • 19
  • [ 2212-75-1 ]
  • [ 2212-69-3 ]
Reference: [1] Justus Liebigs Annalen der Chemie, 1964, vol. 674, p. 218 - 225
  • 20
  • [ 383-63-1 ]
  • [ 2212-75-1 ]
  • [ 14905-30-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2001, vol. 44, # 16, p. 2636 - 2660
[2] European Journal of Organic Chemistry, 2017, vol. 2017, # 25, p. 3606 - 3611
[3] Patent: US2007/275906, 2007, A1, . Location in patent: Page/Page column 30-31
  • 21
  • [ 2212-75-1 ]
  • [ 14905-30-7 ]
Reference: [1] Patent: US6057295, 2000, A,
  • 22
  • [ 2212-75-1 ]
  • [ 407-25-0 ]
  • [ 14905-30-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 21, p. 5235 - 5243
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