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[ CAS No. 36061-08-2 ] {[proInfo.proName]}

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Chemical Structure| 36061-08-2
Chemical Structure| 36061-08-2
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Product Details of [ 36061-08-2 ]

CAS No. :36061-08-2 MDL No. :MFCD03844654
Formula : C11H15NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :XOQZTHUXZWQXOK-SNVBAGLBSA-N
M.W : 193.24 Pubchem ID :6993756
Synonyms :

Calculated chemistry of [ 36061-08-2 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.36
Num. rotatable bonds : 5
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 55.12
TPSA : 63.32 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -7.73 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.75
Log Po/w (XLOGP3) : -0.36
Log Po/w (WLOGP) : 1.42
Log Po/w (MLOGP) : -0.52
Log Po/w (SILICOS-IT) : 1.59
Consensus Log Po/w : 0.78

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 1.0
Bioavailability Score : 0.55

Water Solubility

Log S (ESOL) : -0.8
Solubility : 30.7 mg/ml ; 0.159 mol/l
Class : Very soluble
Log S (Ali) : -0.51
Solubility : 60.1 mg/ml ; 0.311 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -2.68
Solubility : 0.406 mg/ml ; 0.0021 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.77

Safety of [ 36061-08-2 ]

Signal Word:Warning Class:
Precautionary Statements:P280-P305+P351+P338 UN#:
Hazard Statements:H302-H312-H315-H319 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 36061-08-2 ]

* 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.

  • Downstream synthetic route of [ 36061-08-2 ]

[ 36061-08-2 ] Synthesis Path-Downstream   1~11

  • 1
  • [ 36061-08-2 ]
  • [ 64-17-5 ]
  • D-2-amino-5-phenylpentanoic acid ethyl ester hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
92% With hydrogenchloride 4 Reflux was resumed the next morning for-1 hour and then 50 mLs of ethyl acetate was added to the vessel. The solution was then concentrated down to-30 mLs via atmospheric distillation. This sequence (i. e. addition of ethyl acetate followed by atmospheric concentration) was repeated twice more before a final addition of 30 mL of ethyl acetate to the warm mixture. The solution was cooled slowly to room temperature (over several hours) and the resulting slurry was stirred at room temperature for 40 minutes. Subsequent filtration and rinsing (once with 10 mLs of cold ethyl acetate), followed by vacuum drying at 50°C, yielded 2.47 grams (-92%) of the title compound. 'H nmr (DMSO-d6) : 8 1.15-1. 21 (t, 3H), 1.50-1. 89 (m, 4H), 2.48-2. 67 (m, 2H), 3.92- 3.98 (t, 1H), 4.08-4. 25 (m, 2H), 7.12-7. 29 (m, 5H), 8.76 (s, broad, 3H).
  • 2
  • [ 108019-30-3 ]
  • [ 36061-08-2 ]
YieldReaction ConditionsOperation in experiment
47.29% With hydrogenchloride; potassium hydroxide; water at 40℃; for 12h; 3 A solution consisting of (DL)-N-acetyl-2-amino-5-phenylpentanoic acid (10.0 grams, 0.043 moles), zinc chloride (0.003 grams), 2 N potassium hydroxide solution (21.5 mL, 0.043 moles), and water (128.5 mL) was adjusted to a pH of 8.0 by the addition concentrated hydrochloric acid. To the reaction mixture was added D-aminoacylase (N- Acyl-D-amino acid amidohydrolase, 0.1 grams) which was then vigorously stirred for 12 hours at 40 °C while maintaining a pH of 8.0 by the addition of 2N potassium hydroxide and concentrated hydrochloric acid. The product was isolated by filtration, washed with heptane (20 mL) and dried in vacuum at 50 ° C to give 3.89 grams (47.29%) of the above-identified product, (D)-N-amino-5-phenylpentanoic acid :'H nmr (TFA-D) : 8 1.906-1. 942 (m, 2H), 2.134-2. 192 (m, 2H), 2.74-2. 786 (m, 2H), 4.352-4. 373 (m, 1H), 7.161-7. 320 (m, 5H), 11.601 (s, 6H).
YieldReaction ConditionsOperation in experiment
89% Stage #1: With palladium 10% on activated carbon; hydrogen In tetrahydrofuran; ethanol at 25℃; for 2h; Stage #2: With trifluoroacetic acid In dichloromethane at 25℃; for 1h; 2 Synthesis of 2-amino-5-phenylvaleric acid General procedure: Under nitrogen, add iodobenzene (2.04g, 10mmol), N-tert-butoxycarbonyl-propargylglycine (2.13g, 10mmol), CuCl (0.04g, 0.40mmol), and dissolve in 40mL of tetrahydropyrrole,Then Pd(PPh3)2Cl2 (0.14g, 0.2mmol) was added, and the reaction was stirred at room temperature (25°C) for 1h. After the reaction was completed, it was extracted with ethyl acetate, dried over anhydrous sodium sulfate, and most of the solvent was removed by spinning off. Analyze and purify, eluting with petroleum ether/ethyl acetate (V/V=15/1) to obtain 2-((tert-butoxycarbonyl)amino)-5-phenyl-4-pentynoic acid (2.6g), Then add 10% Pd/C (1.16g) dissolved in a mixed solution of EtOH (15mL) and THF (15mL), react under H2 at room temperature (25) for 2h, after removing the solvent, add 20% (V /V) In TFA/CH2Cl2 (30mL), the reaction mixture was stirred at room temperature (25°C) for 1h, the aqueous phase was extracted three times with ethyl acetate, the organic phases were combined, dried over anhydrous sodium sulfate, and most of the solvent was removed by spin-off and reconstituted with n-hexane. Crystallized to obtain 2-amino-5-phenylvaleric acid (2.57 g) with a yield of 89%.
5.C C. C. 2-(R)-Amino-5-phenyl-pentanoic acid A mixture of 440 mg (1.19 mmol) of 5B and 120 mg of palladium chloride in 20 mL of ethanol and 10 mL of THF was hydrogenated at 45 psi. for about 16 h. The mixture was filtered through diatomaceous earth and concentrated, and the residue was triturated with ether to give 240 mg of 5C as a white solid.
5.C C. C. 2-(R)-Amino-5-phenyl-pentanoic acid A mixture of 440 mg (1.19 mmol) of 5 B and 120 mg of palladium chloride in 20 mL of ethanol and 10 mL of THF was hydrogenated at 45 psi. for about 16 h. The mixture was filtered through diatomaceous earth and concentrated, and the residue was triturated with ether to give 240 mg of 5 C as a white solid.
  • 4
  • N-[(1,1-dimethylethoxy)carbonyl]amino-(2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate [ No CAS ]
  • [ 4392-24-9 ]
  • [ 36061-08-2 ]
YieldReaction ConditionsOperation in experiment
With sodium hexamethyldisilazane; trifluoroacetic acid In tetrahydrofuran; ethanol; hexane; dichloromethane; sodium hydrogencarbonate 73.A (2R)-2-amino-5-phenyl-pentanoic acid Step A (2R)-2-amino-5-phenyl-pentanoic acid To a stirred solution of N-[(1,1-dimethylethoxy)carbonyl]amino-(2S,3R)-(+)-6-oxo-2,3-diphenyl-4-morpholinecarboxylate, (1.0 g, 2.8 mmol) and cinnamyl bromide (2.78 g, 14 mmol) in dry THF (70 mL) at -78° C., was added dropwise sodium hexamethyldisilazide (5.6 mL; 1.0M solution in hexane). The reaction mixture was stirred for 30 minutes, then poured into ethyl acetate (150 mL) and washed with brine, dried over anhydrous magnesium sulfate, filtered and evaporated. The crude product was first washed with warm hexane and then with an ether:hexane (1:1) mixture. The solid material was the desired product. A solution of this intermediate (1.0 g, 2.1 mmol) in CH2 Cl2 (2 mL) and TFA (2 mL) was stirred at room temperature for 1 h. The solvents were removed under reduced pressure and the residue was dissolved in saturated aqueous sodium bicarbonate solution and extracted with CHCl3. The organic layer was washed with brine, dried over potassium carbonate, filtered and evaporated to give the amine as a foam which was used without purification. Approximately 0.6 g (1.62 mmol) of this material was dissolved in 40 mL of (2:1) EtOH:THF and hydrogenated under 40 psi using PdCl2 /C for 24 h. The catalyst was filtered off through celite pad and the solvent was evaporated to give the title compound as a colorless solid. 1 H NMR (400MHz, CD3 OD) δ7.2 (m, 5H), 3.77 (t, 1H), 2.6 (t, 2H), 1.9 (m, 4H).
  • 5
  • [ 36061-08-2 ]
  • [ 103290-07-9 ]
  • [ 159635-47-9 ]
YieldReaction ConditionsOperation in experiment
With triethylamine In 1,4-dioxane; water 199.C C. C. 2(R)-(2-Tert-Butoxycarbonylamino-2-Methyl-Propionylamino)-5-Phenyl-Pentanoic Acid To a solution of the compound of Example 199, Step B (130 mg, 0.67 mmol) in dioxane:water (4:1, 5 mL) was added triethylamine (0.28 mL, 2 mmol) and Example 1, Step D (201 mg, 0.67 mmol). The mixture was stirred at 45° C. for 16 h, diluted with EtOAc (20 mL) and water (10 mL) and acidified to pH 2 with HOAc. The organic phase was collected, washed with saturated NaHCO3 and brine solutions, dried over MgSO4 and concentrated to quantitatively give crude Example 199, Step C (298 mg): +APcl MS (M+1)+379, (M-tBu+1)+323, (M-Boc+1)+279; 1H NMR=400 MHz (CDCl3) δ: 7.21 (m, 2H), 7.14 (m, 3H), 4.51 (m, 1H), 1.38 (s, 9H).
  • 6
  • C2HF3O2*C12H17NO2 [ No CAS ]
  • [ 36061-08-2 ]
YieldReaction ConditionsOperation in experiment
99% With hydrogenchloride In water at 80℃; for 6h; optical yield given as %ee;
  • 7
  • [ 130047-14-2 ]
  • [ 36061-08-2 ]
  • [ 1021707-70-9 ]
YieldReaction ConditionsOperation in experiment
Stage #1: (2R)-2-amino-5-phenylpentanoic acid With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine In dichloromethane for 1h; Reflux; Stage #2: 4-[(chlorosulfonyl)methyl]benzoic acid methyl ester With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; for 1.75h; 2.1.g 1.3 g (6.72 mmol) of H-d-Ppg-OH (Peptech, Burlington, Mass.) were suspended in 90 ml of dry DCM, and 2 ml (15.7 mmol) of TMS-Cl and 2.6 ml (15 mmol) of DIEA were added. The mixture was refluxed for 1 h, the clear solution was cooled to 0° C., and 2 g (8 mmol) of 3-MeOOC-Bzls-Cl and 2.6 ml of DIEA were added. The mixture was stirred at 0° C. for 15 min and at RT for 1.5 h. The solvent was removed in vacuo, and the residue was dissolved in 700 ml of half-saturated NaHCO3 solution. The mixture was extracted 2× with a little ethyl acetate, and then the aqueous phase was acidified with HCl (pH about 2-3). The mixture is extracted 3× with 150 ml of ethyl acetate, and the combined ethyl acetate phase is washed 2× with 5% KHSO4 solution and 1× with saturated NaCl solution. The organic phase is dried with Na2SO4, and the solvent is removed in vacuo.Yield: 2.4 g of oil (HPLC: 33.53 min, Start with 20% B)
  • 8
  • [ 36061-08-2 ]
  • [ 1939-99-7 ]
  • [ 1322746-50-8 ]
YieldReaction ConditionsOperation in experiment
75% With sodium hydroxide In 1,4-dioxane; water at 0 - 20℃; [0091] Bzls-DPpg-OH; [0092] To a mixture of DPpg (3 g, 15 mmol) in aqueous 1M NaOH (15 ml, 15 mmol), dioxane (100 ml) and water (30 ml) was added in parallel a solution of Bzls-chloride (4.4 g, 23 mmol) in dioxane (10 ml) and aqueous 1M NaOH (25 ml, 25 mmol) at 0 °C over a period of 60 min. The pH was maintained between 8-9 by addition of aqueous 1M NaOH. The mixture was stirred at room temperature overnight. Additional Bzls-chloride (6 g, 31 mmol) and aqueous 1M NaOH (31 ml, 31 mmol) was added at 0 °C in portions and the pH maintained between 8-9 by addition of aqueous 1M NaOH. Stirring was continued until no more starting material was detected by TLC. The solvent was evaporated in vacuo and the residue portioned between ethyl acetate and aqueous 5 % KHS04. The organic layer was washed with aqueous 5 % KHSO4 and brine, dried (Na2S04), and evaporated in vacuo to afford the title compound.Yield: 4 g (75 %, white solid).Anal. HPLC: 69.3 % B; MS calc: 347.1, found 346.3 (M-H)~ [0093] (3-MeOOC)Bzls-DPpg-OH
  • 9
  • [ 36061-08-2 ]
  • C44H50N6O8S [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 2 steps 1: sodium hydroxide / 1,4-dioxane; water / 0 - 20 °C / pH 8 - 9 2: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0 - 20 °C
  • 10
  • [ 36061-08-2 ]
  • Bzls-DPpg-hAla(4-Pip)-4-Amba x 2TFA [ No CAS ]
YieldReaction ConditionsOperation in experiment
Multi-step reaction with 3 steps 1.1: sodium hydroxide / 1,4-dioxane; water / 0 - 20 °C / pH 8 - 9 2.1: N-ethyl-N,N-diisopropylamine; benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate / N,N-dimethyl-formamide / 0 - 20 °C 3.1: hydrogen / palladium 10% on activated carbon / water; acetic acid / 20 °C / Inert atmosphere 3.2: 1 h / 20 °C 3.3: Chromatography
  • 11
  • [ 36061-08-2 ]
  • methyl 3-[(chlorosulfonyl)methyl]benzoate [ No CAS ]
  • [ 1021707-70-9 ]
YieldReaction ConditionsOperation in experiment
88% Stage #1: (2R)-2-amino-5-phenylpentanoic acid With chloro-trimethyl-silane; N-ethyl-N,N-diisopropylamine In dichloromethane for 1h; Reflux; Stage #2: methyl 3-[(chlorosulfonyl)methyl]benzoate With N-ethyl-N,N-diisopropylamine In dichloromethane at 0 - 20℃; [0093] (3-MeOOC)Bzls-DPpg-OH; [0094] To a suspension of DPpg (1.3 g, 6.7 mmol) in dry DCM (90 ml) was added TMS-C1 (2 ml, 15.7 mmol) and DIEA (2.6 ml, 15 mmol) at room temperature and the mixture was refluxed for 1 h with stirring. The clear solution was cooled to 0°C and (3-MeOOC)Bzls- chloride (2 g, 8 mmol) and DIEA (2.6 ml) was added. The mixture was stirred at 0°C for 15 min and at room temperature for 1.5 h. The solvent was evaporated in vacuo and the residue dissolved in half- saturated aqueous NaHC03 (700 ml) followed by extraction with ethyl acetate. The aqueous layer was acidified with aqueous HC1 (pH about 2-3) and extracted with ethyl acetate. The organic layer was washed with aqueous 5% KHS04 and brine, dried (Na2S04), and evaporated in vacuo to afford the title compound.Yield: 2.4 g (88 %, amorphous yellow solid).Anal. HPLC: 69.2 min % B; MS calc: 405.1, found 404.3 (M-H)~
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