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[ CAS No. 13512-31-7 ] {[proInfo.proName]}

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Chemical Structure| 13512-31-7
Chemical Structure| 13512-31-7
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Product Details of [ 13512-31-7 ]

CAS No. :13512-31-7 MDL No. :MFCD00038784
Formula : C18H19NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :SLLMDHBKALJDBW-INIZCTEOSA-N
M.W : 329.35 Pubchem ID :7010613
Synonyms :

Calculated chemistry of [ 13512-31-7 ]

Physicochemical Properties

Num. heavy atoms : 24
Num. arom. heavy atoms : 12
Fraction Csp3 : 0.22
Num. rotatable bonds : 9
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 87.71
TPSA : 84.86 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) : -6.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.47
Log Po/w (XLOGP3) : 2.23
Log Po/w (WLOGP) : 2.25
Log Po/w (MLOGP) : 2.17
Log Po/w (SILICOS-IT) : 2.46
Consensus Log Po/w : 2.31

Druglikeness

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

Water Solubility

Log S (ESOL) : -3.06
Solubility : 0.285 mg/ml ; 0.000865 mol/l
Class : Soluble
Log S (Ali) : -3.65
Solubility : 0.0742 mg/ml ; 0.000225 mol/l
Class : Soluble
Log S (SILICOS-IT) : -4.99
Solubility : 0.00339 mg/ml ; 0.0000103 mol/l
Class : Moderately soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.07

Safety of [ 13512-31-7 ]

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 [ 13512-31-7 ]

* 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.

  • Upstream synthesis route of [ 13512-31-7 ]
  • Downstream synthetic route of [ 13512-31-7 ]

[ 13512-31-7 ] Synthesis Path-Upstream   1~19

  • 1
  • [ 1080-06-4 ]
  • [ 501-53-1 ]
  • [ 13512-31-7 ]
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 20, p. 6347 - 6355
[2] Journal of Organic Chemistry, 1997, vol. 62, # 12, p. 3880 - 3889
[3] Angewandte Chemie - International Edition, 2003, vol. 42, # 15, p. 1753 - 1758
[4] Synthetic Communications, 2003, vol. 33, # 23, p. 4019 - 4027
[5] Journal of the American Chemical Society, 2007, vol. 129, # 51, p. 15830 - 15838
[6] Biochemical Journal, 1954, vol. 57, p. 538,539
[7] Tetrahedron Letters, 1994, vol. 35, # 45, p. 8397 - 8400
[8] Tetrahedron Letters, 1995, vol. 36, # 33, p. 5963 - 5966
[9] Angewandte Chemie - International Edition, 2001, vol. 40, # 10, p. 1967 - 1970
[10] Angewandte Chemie - International Edition, 2002, vol. 41, # 3, p. 512 - 515
[11] Bioorganic and Medicinal Chemistry, 2010, vol. 18, # 24, p. 8679 - 8686
[12] Patent: WO2011/106898, 2011, A1, . Location in patent: Page/Page column 19
  • 2
  • [ 3417-91-2 ]
  • [ 501-53-1 ]
  • [ 13512-31-7 ]
YieldReaction ConditionsOperation in experiment
390 g With sodium carbonate In water; ethyl acetate To the above-obtained solid Tyr-OMe · HCl (tyrosine hydrochloride), 300 g of AcOEt (ethyl acetate) was added, 100 g of Na2CO3 (sodium carbonate) was added with stirring, 50 g of water was added,And 230 g of Z-Cl (benzyl chloroformate) was slowly added dropwise.Control system pH = 8, by TLC (thin layer chromatography) to the reaction system without Tyr-OMe · HCl (tyrosine hydrochloride), after adding citric acid, acidified to pH = 3, static layer , The ester layer was washed with salt water as neutral.The ester layer was added with 20 ~ 50g anhydrous Na2SO4 (anhydrous sodium sulfate), stirred and dried for 4 hours. Na2SO4 (sodium sulfate) was removed by filtration. The filtrate was concentrated and then added to a crystallization kettle. The hot water was concentrated to dryness.Add PET (petroleum ether) 200g, stirring crystallization is completed.The white crystals of the white crystals Z-L-Tyr-OMe (N-benzyloxycarbonyl-L-tyrosine methyl ester) were filtered and dried to dryness to dryness of 390 g and water at 4percent.
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 32, p. 10162 - 10173
[2] Croatica Chemica Acta, 2003, vol. 76, # 1, p. 23 - 36
[3] Journal of Organic Chemistry, 1986, vol. 51, # 14, p. 2728 - 2735
[4] Journal of the American Chemical Society, 2004, vol. 126, # 40, p. 12897 - 12906
[5] Patent: CN103833593, 2016, B, . Location in patent: Paragraph 0045; 0047
[6] Journal of Medicinal Chemistry, 2018, vol. 61, # 17, p. 7929 - 7941
  • 3
  • [ 67-56-1 ]
  • [ 1164-16-5 ]
  • [ 13512-31-7 ]
YieldReaction ConditionsOperation in experiment
96% at 70℃; for 2 h; 3..
methyl (2S)-3-(4-hydroxyphenyl)-2-[(phenylmethoxy)carbonyl amino]propanoate
To a solution of 15.6 g (49 mmol) (2S)-3-(4-hydroxyphenyl)-2-[(phenylmethoxy)carbonylamino]propanoic acid in 120 ML methanol was added 9.4 g (49 mmol) of p-toluenesulfonic acid monohydrate..
The solution was heated to 70 ° C. for 2 h..
After solution was cooled to room temperature, the methanol was removed under reduced pressure..
The solid obtained was redissolved in 120 ML methylene chloride..
The organic solution was then washed with dilute NaHCO3 solution twice and brine..
The organic layer was dried with anhydrous MgSO4 and filtered..
The solvent was removed under reduced pressure..
The crude mixture was chromatographed on a silica gel column using 40percent ethyl acetate in hexanes as the eluent to yield 15.6 g (96percent) of white solid as product: 1H NMR (300 MHz, CDCl3) δ7.38-7.30 (m, 5H), 6.93 (d, J=8.41 Hz, 2H), 6.81 (d, J=8.41 Hz, 2H), 5.39 (br s, 1H), 5.24 (d, J=9.29 Hz, 1H), 5.11 (d, J=12.32 Hz, 1H), 5.06 (d, J=12.29 Hz, 1H), 4.61 (m, 1H), 3.71 (s, 3H), 3.06 (dd, J=5.88, 14.06 Hz, 1H), 2.98 (dd, J=5.88, 14.06 Hz, 1H)
86% for 12 h; Inert atmosphere; Reflux To a solution of N-Cbz-L-tyrosine (10.0 g, 31.7 mmol) in 100 mL of anhydrous MeOH was added 1 mL of concentrated sulfuric acid and the resulting mixture was heated at reflux overnight. The solution was then cooled to room temperature and concentrated under reduced pressure. The residue was diluted in 30 mL Et2O was added and washed successively with 5percent aqueous NaHCO3, brine, and finally dried over MgSO4. After drying under vacuum 5 was obtained as a pale yellow resin (9.0 g, 86 percent). 1H NMR (500 MHz, CDCl3) δ 7.35 (m, 5H), 6.96 (d, J = 8.2 Hz, 2H), 6.72 (d, J = 8.2 Hz, 2H), 5.69 (bs, 1H; OH), 5.29 (d, J = 8.2 Hz, 1H; NH), 5.14 (d, JAB = 12.2, 1H), 5.10 (d, JAB = 12.2, 1H), 4.65 (m, 1H), 3.75 (s, 3H), 3.08 (dd, J = 5.5 Hz, JAB = 14.0 Hz, 1H), 3.02 (dd, J = 5.5 Hz, JAB = 14.0 Hz, 1H). 13C NMR (127 MHz, CDCl3) δ 172.3, 155.8, 155.0, 136.1, 130.4, 128.6, 128.3, 128.1, 127.4, 115.6, 67.1, 55.0, 52.4, 37.5.
Reference: [1] Patent: US6344484, 2002, B1, . Location in patent: Page column 29-30
[2] Organic Letters, 2012, vol. 14, # 5, p. 1330 - 1333
[3] Chemical Communications, 2014, vol. 50, # 88, p. 13608 - 13611
[4] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 17, p. 5407 - 5413
[5] Bulletin of the Chemical Society of Japan, 1978, vol. 51, # 6, p. 1897 - 1898
  • 4
  • [ 67-56-1 ]
  • [ 5618-98-4 ]
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Reference: [1] Organic Letters, 2009, vol. 11, # 3, p. 765 - 768
  • 5
  • [ 13139-17-8 ]
  • [ 3417-91-2 ]
  • [ 13512-31-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2004, vol. 47, # 16, p. 4041 - 4053
[2] Bioorganic and Medicinal Chemistry, 2003, vol. 11, # 24, p. 5449 - 5460
  • 6
  • [ 60-18-4 ]
  • [ 13512-31-7 ]
Reference: [1] Journal of the American Chemical Society, 2004, vol. 126, # 20, p. 6347 - 6355
[2] Croatica Chemica Acta, 2003, vol. 76, # 1, p. 23 - 36
[3] Angewandte Chemie - International Edition, 2002, vol. 41, # 3, p. 512 - 515
[4] Angewandte Chemie - International Edition, 2001, vol. 40, # 10, p. 1967 - 1970
[5] Tetrahedron Letters, 1994, vol. 35, # 45, p. 8397 - 8400
[6] Patent: WO2011/106898, 2011, A1,
[7] Patent: CN103833593, 2016, B,
  • 7
  • [ 1164-16-5 ]
  • [ 74-88-4 ]
  • [ 13512-31-7 ]
Reference: [1] Synlett, 2010, # 20, p. 3081 - 3085
[2] ChemMedChem, 2015, vol. 10, # 3, p. 498 - 510
  • 8
  • [ 1164-16-5 ]
  • [ 74-88-4 ]
  • [ 13512-31-7 ]
Reference: [1] Patent: US5741796, 1998, A,
  • 9
  • [ 1164-16-5 ]
  • [ 4637-24-5 ]
  • [ 13512-31-7 ]
Reference: [1] Chemical and Pharmaceutical Bulletin, 2003, vol. 51, # 3, p. 320 - 324
  • 10
  • [ 67-56-1 ]
  • [ 205866-50-8 ]
  • [ 13512-31-7 ]
Reference: [1] Tetrahedron Letters, 2001, vol. 42, # 31, p. 5319 - 5321
  • 11
  • [ 13139-17-8 ]
  • [ 1080-06-4 ]
  • [ 13512-31-7 ]
Reference: [1] Synthesis, 2009, # 22, p. 3765 - 3768
  • 12
  • [ 67-56-1 ]
  • [ 19898-39-6 ]
  • [ 1164-16-5 ]
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Reference: [1] Advanced Synthesis and Catalysis, 2014, vol. 356, # 10, p. 2197 - 2202
  • 13
  • [ 186581-53-3 ]
  • [ 1164-16-5 ]
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Reference: [1] Heterocycles, 1981, vol. 15, # 2, p. 1205 - 1208
  • 14
  • [ 1080-06-4 ]
  • [ 13795-24-9 ]
  • [ 13512-31-7 ]
Reference: [1] Journal of Medicinal Chemistry, 2006, vol. 49, # 25, p. 7493 - 7501
  • 15
  • [ 67-56-1 ]
  • [ 7278-35-5 ]
  • [ 13512-31-7 ]
Reference: [1] Journal of the Chemical Society, Perkin Transactions 1: Organic and Bio-Organic Chemistry (1972-1999), 1988, p. 535 - 540
  • 16
  • [ 13512-31-7 ]
  • [ 115-11-7 ]
  • [ 5545-54-0 ]
Reference: [1] Patent: CN103833593, 2016, B, . Location in patent: Paragraph 0045; 0048
  • 17
  • [ 13512-31-7 ]
  • [ 5545-54-0 ]
Reference: [1] Croatica Chemica Acta, 2003, vol. 76, # 1, p. 23 - 36
  • 18
  • [ 13512-31-7 ]
  • [ 3417-91-2 ]
Reference: [1] Journal of Organic Chemistry, 2007, vol. 72, # 17, p. 6599 - 6601
  • 19
  • [ 13512-31-7 ]
  • [ 71989-38-3 ]
Reference: [1] Patent: CN103833593, 2016, B,
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