Home Cart 0 Sign in  

[ CAS No. 37169-36-1 ] {[proInfo.proName]}

,{[proInfo.pro_purity]}
Cat. No.: {[proInfo.prAm]}
Chemical Structure| 37169-36-1
Chemical Structure| 37169-36-1
Structure of 37169-36-1 * Storage: {[proInfo.prStorage]}
Cart0 Add to My Favorites Add to My Favorites Bulk Inquiry Inquiry Add To Cart

Quality Control of [ 37169-36-1 ]

Related Doc. of [ 37169-36-1 ]

Alternatived Products of [ 37169-36-1 ]

Product Details of [ 37169-36-1 ]

CAS No. :37169-36-1 MDL No. :MFCD20260285
Formula : C15H21NO6 Boiling Point : -
Linear Structure Formula :- InChI Key :VURIGNDVTSFLOU-JTQLQIEISA-N
M.W :311.33 Pubchem ID :14889488
Synonyms :
(S)-Methyl 2-((tert-butoxycarbonyl)amino)-3-(3,4-dihydroxyphenyl)propanoate

Calculated chemistry of [ 37169-36-1 ]

Physicochemical Properties

Num. heavy atoms : 22
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.47
Num. rotatable bonds : 8
Num. H-bond acceptors : 6.0
Num. H-bond donors : 3.0
Molar Refractivity : 79.71
TPSA : 105.09 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) : -7.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.46
Log Po/w (XLOGP3) : 1.43
Log Po/w (WLOGP) : 1.71
Log Po/w (MLOGP) : 1.14
Log Po/w (SILICOS-IT) : 1.28
Consensus Log Po/w : 1.6

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.34
Solubility : 1.41 mg/ml ; 0.00452 mol/l
Class : Soluble
Log S (Ali) : -3.24
Solubility : 0.178 mg/ml ; 0.000573 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.71
Solubility : 0.604 mg/ml ; 0.00194 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 1.0 alert
Brenk : 2.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.01

Safety of [ 37169-36-1 ]

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 [ 37169-36-1 ]

* 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 [ 37169-36-1 ]
  • Downstream synthetic route of [ 37169-36-1 ]

[ 37169-36-1 ] Synthesis Path-Upstream   1~22

  • 1
  • [ 24424-99-5 ]
  • [ 1421-65-4 ]
  • [ 37169-36-1 ]
YieldReaction ConditionsOperation in experiment
85% With sodium hydrogencarbonate In tetrahydrofuran; water at 20℃; for 1 h; Toan ice-cold solution of 6 (0.9 g,3.6 mmol) in THF (6.5 mL), a saturated aqueous solution of NaHCO3(6.5 mL) and a solution of di-tert-butyl-dicarbonate (0.87 g, 4.0 mmol) in THF (4.0 mL) were addedsuccessively. The resulting reaction mixture was stirredat ambient temperature for 1 h and then evaporated to remove organic solvent.The aqueous phase was extracted thrice with CH2Cl2. Thecombined organic layers were washed with brine, dried over Na2SO4and evaporated to dryness. The residue was triturated with Et2O andrefrigerated. Compound 7was obtainedafter filtration under vacuo.
76% With sodium hydrogencarbonate In tetrahydrofuran; water for 1.5 h; Cooling with ice DOPA-OMe hydrochloride (1.26 g, 5.11 mmol) was dissolved in tetrahydrofuran (10 ml), saturated aqueous sodium bicarbonate solution (8 ml) was added, and the mixture was cooled in an ice bath. To this solution was added BocO (1.00 ml, 4.35 mmol), and the mixture was warmed to room temperature and stirred for 1.5 hr. The reaction mixture was concentrated under reduced pressure, and dichloromethane (10 ml) and water (5 ml) were added to the residue, and the mixture was extracted twice with dichloromethane. The organic layer was washed with 10percent aqueous citric acid solution (10 ml) and then with 15percent brine (10 ml), and dried over magnesium sulfate. The desiccant was filtered off, and the filtrate was concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (gradient; hexane:ethyl acetate=9:1→1:1) to give Boc-DOPA-OMe (980 mg, 3.15 mmol, yield 76percent) as a pale-peach candy-like substance. (0198) 1H-NMR (400 MHz,CDCl3) δ: 1.42 (s, 9H), 2.89-3.01 (m, 2H), 3.71 (s, 3H), 4.49-4.54 (m, 1H), 5.01 (d, 1H, J=8.0 Hz), 5.51 (s, 1H), 5.65 (s, 1H), 6.54 (dd, 1H, J=1.5, 8.0 Hz), 6.65 (br, 1H), 6.76 (d, 1H, J=8.1 Hz). (0199) ESIMS (m/z) : 310.0 ([M−H]).
Reference: [1] Tetrahedron Asymmetry, 2005, vol. 16, # 4, p. 857 - 864
[2] Chemistry - A European Journal, 2014, vol. 20, # 31, p. 9519 - 9523
[3] European Journal of Medicinal Chemistry, 2010, vol. 45, # 9, p. 4035 - 4042
[4] Journal of Heterocyclic Chemistry, 2006, vol. 43, # 1, p. 139 - 148
[5] European Journal of Organic Chemistry, 2007, # 31, p. 5212 - 5225
[6] Chemical Research in Toxicology, 2010, vol. 23, # 1, p. 211 - 219
[7] Bioorganic Chemistry, 2016, vol. 66, p. 132 - 144
[8] Patent: US2016/200755, 2016, A1, . Location in patent: Page/Page column 9
[9] Synthesis (Germany), 2017, vol. 49, # 12, p. 2691 - 2699
[10] Supramolecular Chemistry, 2018, vol. 30, # 3, p. 184 - 195
  • 2
  • [ 67-56-1 ]
  • [ 24424-99-5 ]
  • [ 59-92-7 ]
  • [ 37169-36-1 ]
YieldReaction ConditionsOperation in experiment
85%
Stage #1: at 20℃; for 24 h; Cooling with ice
Stage #2: at 20℃; for 2 h;
thionyl chloride (15 mL, 95.68 mmol) was added to L-Dopa (14.5 g, 73.6 mmol) under ice-In 100 mL of methanol,The reaction was carried out at room temperature with stirring for 24 hours,After the completion of the reaction, the reaction solution is distilled under reduced pressure to remove the solvent methanol in the reaction solution to obtain the product;The resulting product was dissolved in 100 mL of saturated sodium bicarbonate and the pH of the product solution was 7 to 8 and then, within 1 hour,Di-t-butyldicarbonate Boc2O (20 g, 91.6 mmol) in 120 mL of THF was added dropwise to the product solution and reacted at room temperature for 2 hours with stirring. After completion of the reaction, the solvent THF was distilled off, the resulting aqueous phase was adjusted to pH 2 and extracted three more times with dichloromethane (PH = 7) to give a multiphase liquid containing both water and organic phases, and the aqueous phase was removed successively with anhydrous magnesium sulphate and the organic phase was washed with saturated brine to neutral (pH = 7) The solvent was removed by concentration of dichloromethane to give compound 2 (18.9 g, 85percent yield).
Reference: [1] Organic and Biomolecular Chemistry, 2017, vol. 15, # 27, p. 5797 - 5804
[2] Patent: CN106187800, 2016, A, . Location in patent: Paragraph 0022; 0069; 0070; 0071; 0072; 0073
  • 3
  • [ 24424-99-5 ]
  • [ 7101-51-1 ]
  • [ 37169-36-1 ]
YieldReaction ConditionsOperation in experiment
90% With sodium hydrogencarbonate In tetrahydrofuran at 0 - 20℃; for 2 h; Example Ib - formation of HO-DOP A-NH-Boc-COOMe (Figure 25B) The yellow powder of example Ia(1.000 g, 4.74 mmol) was dissolved in tetrahydrofuran (10 ml) and a solution of IM NaHCO3 (10.0 ml, 10.0 mmol) was added. The resulting solution was cooled at 00C, and di-tertbutyl-dicarbonate (1.093 g., 5.0 mmol) was added slowly. The solution was stirred at 00C for 1 hour, and then warmed to room temperature and it was stirred for another one hours at room temperature. The organic solvent was removed by vacuum and the aqueous layer was extracted using ethyl acetate (3x10 ml). All organic fractions were combined. The organic layer was washed respectively with water (2x20 ml), 5percent HCl (2x20 ml), water (20 ml), brine (20 ml), and dried over MgSψ4 and the solvent was removed using vacuum. Further purification was performed using flash chromatography with the eluent: 1 : 1 ethyl acetate hexane. The pure product was retrieved as a white solid (1.315 g.).
Reference: [1] Chemical Communications, 2011, vol. 47, # 38, p. 10746 - 10748
[2] Patent: WO2007/87256, 2007, A2, . Location in patent: Page/Page column 20; 23; sheet 17
[3] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 6, p. 2051 - 2066
[4] Organic Letters, 2006, vol. 8, # 20, p. 4421 - 4424
[5] Patent: WO2007/87256, 2007, A2, . Location in patent: Page/Page column 28
[6] Synlett, 2012, # 4, p. 565 - 568
[7] Patent: CN107848954, 2018, A, . Location in patent: Paragraph 0083
  • 4
  • [ 24424-99-5 ]
  • [ 37169-36-1 ]
Reference: [1] Patent: US6576766, 2003, B1,
  • 5
  • [ 2577-48-2 ]
  • [ 53267-93-9 ]
  • [ 37169-36-1 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 74, p. 60354 - 60364
  • 6
  • [ 59-92-7 ]
  • [ 37169-36-1 ]
Reference: [1] Organic Letters, 2006, vol. 8, # 20, p. 4421 - 4424
[2] Journal of Heterocyclic Chemistry, 2006, vol. 43, # 1, p. 139 - 148
[3] Tetrahedron Asymmetry, 2005, vol. 16, # 4, p. 857 - 864
[4] Bioorganic and Medicinal Chemistry, 2002, vol. 10, # 6, p. 2051 - 2066
[5] Chemical Research in Toxicology, 2010, vol. 23, # 1, p. 211 - 219
[6] Organic Letters, 2013, vol. 15, # 7, p. 1702 - 1705
[7] Chemistry - A European Journal, 2014, vol. 20, # 31, p. 9519 - 9523
[8] Bioorganic Chemistry, 2016, vol. 66, p. 132 - 144
[9] Synthesis (Germany), 2017, vol. 49, # 12, p. 2691 - 2699
[10] Supramolecular Chemistry, 2018, vol. 30, # 3, p. 184 - 195
[11] Patent: CN107848954, 2018, A,
  • 7
  • [ 24424-99-5 ]
  • [ 59-92-7 ]
  • [ 37169-36-1 ]
Reference: [1] Patent: US6521666, 2003, B1,
  • 8
  • [ 10065-72-2 ]
  • [ 53267-93-9 ]
  • [ 37169-36-1 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 74, p. 60354 - 60364
  • 9
  • [ 53267-93-9 ]
  • [ 616-34-2 ]
  • [ 37169-36-1 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 74, p. 60354 - 60364
  • 10
  • [ 2666-93-5 ]
  • [ 53267-93-9 ]
  • [ 37169-36-1 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 74, p. 60354 - 60364
  • 11
  • [ 2577-90-4 ]
  • [ 53267-93-9 ]
  • [ 37169-36-1 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 74, p. 60354 - 60364
  • 12
  • [ 4530-20-5 ]
  • [ 53267-93-9 ]
  • [ 37169-36-1 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 74, p. 60354 - 60364
  • 13
  • [ 15761-38-3 ]
  • [ 53267-93-9 ]
  • [ 37169-36-1 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 74, p. 60354 - 60364
  • 14
  • [ 4326-36-7 ]
  • [ 37169-36-1 ]
Reference: [1] ChemPlusChem, 2013, vol. 78, # 4, p. 325 - 330
[2] Tetrahedron Letters, 2009, vol. 50, # 47, p. 6519 - 6521
[3] Angewandte Chemie - International Edition, 2016, vol. 55, # 38, p. 11543 - 11547[4] Angew. Chem., 2016, vol. 128, p. 11715 - 11719,5
  • 15
  • [ 4070-48-8 ]
  • [ 53267-93-9 ]
  • [ 37169-36-1 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 74, p. 60354 - 60364
  • 16
  • [ 10332-17-9 ]
  • [ 53267-93-9 ]
  • [ 37169-36-1 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 74, p. 60354 - 60364
  • 17
  • [ 13734-41-3 ]
  • [ 53267-93-9 ]
  • [ 37169-36-1 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 74, p. 60354 - 60364
  • 18
  • [ 13139-15-6 ]
  • [ 53267-93-9 ]
  • [ 37169-36-1 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 74, p. 60354 - 60364
  • 19
  • [ 13734-34-4 ]
  • [ 53267-93-9 ]
  • [ 37169-36-1 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 74, p. 60354 - 60364
  • 20
  • [ 15761-39-4 ]
  • [ 53267-93-9 ]
  • [ 37169-36-1 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 74, p. 60354 - 60364
  • 21
  • [ 53267-93-9 ]
  • [ 13139-14-5 ]
  • [ 37169-36-1 ]
Reference: [1] RSC Advances, 2015, vol. 5, # 74, p. 60354 - 60364
  • 22
  • [ 51779-32-9 ]
  • [ 7101-51-1 ]
  • [ 37169-36-1 ]
Reference: [1] Organic Letters, 2013, vol. 15, # 7, p. 1702 - 1705
Same Skeleton Products
Historical Records

Related Functional Groups of
[ 37169-36-1 ]

Amino Acid Derivatives

Chemical Structure| 76757-90-9

[ 76757-90-9 ]

Boc-D-Tyr-OMe

Similarity: 0.97

Chemical Structure| 4326-36-7

[ 4326-36-7 ]

Boc-Tyr-OMe

Similarity: 0.97

Chemical Structure| 18938-60-8

[ 18938-60-8 ]

Boc-Tyr-OtBu

Similarity: 0.96

Chemical Structure| 72594-77-5

[ 72594-77-5 ]

(S)-Ethyl 2-((tert-butoxycarbonyl)amino)-3-(4-hydroxyphenyl)propanoate

Similarity: 0.96

Chemical Structure| 16881-33-7

[ 16881-33-7 ]

tert-Butyl ((benzyloxy)carbonyl)-L-tyrosinate

Similarity: 0.94