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Chemical Structure| 61-90-5
Chemical Structure| 61-90-5
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Product Details of [ 61-90-5 ]

CAS No. :61-90-5 MDL No. :MFCD00002617
Formula : C6H13NO2 Boiling Point : -
Linear Structure Formula :- InChI Key :ROHFNLRQFUQHCH-YFKPBYRVSA-N
M.W : 131.17 Pubchem ID :6106
Synonyms :
Leucine;Leu;AI3-08899;Leucinum;FEMA No. 3297;Pentanoic Acid;NSC 46709;(S)-Leucine

Calculated chemistry of [ 61-90-5 ]

Physicochemical Properties

Num. heavy atoms : 9
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 3
Num. H-bond acceptors : 3.0
Num. H-bond donors : 2.0
Molar Refractivity : 35.44
TPSA : 63.32 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) : -8.18 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.14
Log Po/w (XLOGP3) : -1.52
Log Po/w (WLOGP) : 0.44
Log Po/w (MLOGP) : -1.82
Log Po/w (SILICOS-IT) : -0.15
Consensus Log Po/w : -0.38

Druglikeness

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

Water Solubility

Log S (ESOL) : 0.5
Solubility : 417.0 mg/ml ; 3.18 mol/l
Class : Highly soluble
Log S (Ali) : 0.7
Solubility : 652.0 mg/ml ; 4.97 mol/l
Class : Highly soluble
Log S (SILICOS-IT) : -0.14
Solubility : 96.1 mg/ml ; 0.733 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 1.39

Safety of [ 61-90-5 ]

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 [ 61-90-5 ]

* 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 [ 61-90-5 ]
  • Downstream synthetic route of [ 61-90-5 ]

[ 61-90-5 ] Synthesis Path-Upstream   1~54

  • 1
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  • [ 57-13-6 ]
  • [ 67337-73-9 ]
Reference: [1] Annali di Chimica (Rome, Italy), 1958, vol. 48, p. 1199,1202
  • 2
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  • [ 3190-70-3 ]
YieldReaction ConditionsOperation in experiment
75% at 50℃; for 1 h; HO-Leu-NH2 (10.0 g, 76.2 mmol) was suspended in 150 mL of anhydrous THF and heated to 50° C. Phosgene (20percent in toluene) (76.0 mL, 152.4 mmol) was added to the amino acid suspension. The amino acid dissolved over the course of approx. 1 hr, forming a clear solution. The solution was concentrated on the rotovap, transferred to a beaker, and hexane was added to precipitate the product. The white solid was isolated by filtration and dissolved in toluene. The solution was filtered over a bed of Celite to remove any insoluble material. An excess of hexane was added to the filtrate to precipitate the product. The NCA was isolated by filtration and dried in vacuo. 9.0 g (75percent yield) of Leu NCA was isolated as a white, crystalline solid. 1H NMR (d6-DMSO) δ 9.13 (1H), 4.44 (1H), 1.74 (1H), 1.55 (2H), 0.90 (6H) ppm.
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[4] Patent: US2789973, 1950, ,
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[13] Patent: WO2006/27788, 2006, A1, . Location in patent: Page/Page column 6
[14] Patent: US2789973, 1950, ,
  • 3
  • [ 61-90-5 ]
  • [ 503-38-8 ]
  • [ 3190-70-3 ]
YieldReaction ConditionsOperation in experiment
78.3% at 20℃; for 22 h; General procedure: A two-necked, round-bottomed flask was charged with the requisite amino acid (1 eq.) and dried under high vacuum at ∼30–40 mTorr for >36 h to remove as much residual moisture as possible. The reaction flask was equipped with a reflux condenser topped with a dual-connection glass adapter, with one end connected to a nitrogen source and the other vented to the top of the fume hood (to properly exhaust the HCl vapors generated). Depending on the reaction scale, either a magnetic stir bar or mechanical paddle stirrer was inserted. Anhydrous THF was added to give an amino acid concentration of 0.4–0.5 M. To the resulting heavy suspension was added neat diphosgene (0.6–1.0 eq.; see Tables 2 and 4) in one portion. The reaction was carefully warmed to 55 °C with an oil bath or left to stir at ambient temperature. The reaction was considered complete when all the solids in the reaction dissolved and 1H NMR analysis of a vacuum-dried 0.3-mL aliquot indicated complete conversion to the product. Once at ambient temperature, the reaction mixture was transferred to a clean and dry round-bottomed flask, and concentrated on a rotary evaporator with the water bath maintained between 25 and 30 °C. Fresh anhydrous THF (∼6–8 mL/g of amino acid) was added to dissolve the material before reconcentrating. The crude product was dissolved in a minimal amount of THF (∼4–6 mL/g of amino acid) and transferred to a large precipitation container. Under a blanket of nitrogen, with vigorous mechanical stirring, heptane (6–8 crude volume) was added over 10–30 min to precipitate. The resulting solid was collected by vacuum filtration, washed with additional heptane (1–2 crude volume), and dried in a vacuum oven at room temperature overnight. Anhydrous DCM (∼8–10 mL/g NCA) was added to the material and stirred for 15–30 min under nitrogen in order to dissolve as much of the crude material as possible. Oven-dried celite with a bed height of 2–4 cm was prepared in a sintered glass Buchner funnel, topped with a Whatman glass microfiber filter, and rinsed with anhydrous DCM before use (taking care to avoid cracks in the bed). The DCM-NCA suspension was filtered through the celite bed and then rinsed through with additional anhydrous DCM (3–5 mL/g of NCA). The clear filtrate was concentrated on a rotary evaporator with the water bath maintained at 25–30 °C. Anhydrous THF (∼6–8 mL/g of NCA) was added to dissolve the product before reconcentrating. The material was dissolved in a minimal amount of THF (∼4–6 mL/g of NCA), precipitated with heptane (6–8 crude volume), and collected/dried using the same method as described for the first precipitation. The final product was packaged under either nitrogen or argon in a container that was then sealed in a FoodSaver heat-seal vacuum bag and stored at 78 °C until use.
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  • 6
  • [ 61-90-5 ]
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  • [ 61-90-5 ]
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  • [ 98204-35-4 ]
  • [ 61-90-5 ]
  • [ 443-48-1 ]
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  • [ 56-87-1 ]
  • [ 78-98-8 ]
  • [ 109-08-0 ]
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  • [ 5910-89-4 ]
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  • 10
  • [ 61-90-5 ]
  • [ 7533-40-6 ]
YieldReaction ConditionsOperation in experiment
82%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 5℃; for 16.75 h; Heating / reflux
Stage #2: With water In tetrahydrofuran; diethyl ether
Example 3 Synthesis of Compound 3 Hydrochloride salt; a. Synthesis of intermediate B; To a solution of dry THF (250 ml) was slowly charged lithium aluminum hydride (10.84 g, 0.151 mol) at 0 C over 30 minutes. To this reaction mixture was charged, in portions, L-leucine (25.Og, 0.227 mol) over a period of 45 minutes while maintaining the reaction mixture temperature between 0-5 C to control the vigorous evolution of hydrogen. The resulting reaction mixture was then heated to reflux and maintained at reflux for 16 hours at which time it was cooled to 0-5 C, diluted with diethyl ether (300 ml) and slowly quenched with DI water (12 ml). To the quenched solution was charged 15percent w/v NaOH solution (12 ml) which resulted in the precipitation of a white solid. The slurry was stirred at room temperature for 30 minutes and the white solid was removed by filtration to give a clear organic filtrate which was dried with sodium sulfate (q.s.). The sodium sulfate was removed by filtration and the organic solution was concentrated under reduced pressure to afford intermediate B as a yellow liquid (20 g, 90percent).
59.5%
Stage #1: With lithium aluminium tetrahydride In tetrahydrofuran at 0 - 20℃; for 24.5 h; Heating / reflux
Stage #2: With sodium hydroxide; water In tetrahydrofuran for 0.5 h;
L-Leucinol (LeuOH). Ten grams of L-Leucine (76.2 mmol) was suspended in 100 mL of THF under the nitrogen atmosphere. The suspension was cooled in the ice bath and 4 g of lithium aluminum hydride (100 mmol) was added over a 30 min period. After the addition was complete, the ice bath was removed and the reactant was warmed to room temperature and then refluxed for 24 hours under nitrogen. The reactant was quenched with water (4 mL), then aqueous 15percent of sodium hydroxide (4 mL), and water 12 mL. The solution was stirred for 30 min and white precipitate is filtrated. The filter cake was washed with Dichloromethane and the combined organic layer was dried with sodium sulfate, and concentrated under reduced pressure (8.7 g., 97 percent). The L-leucinol was isolated by distillation. Bp 90 0C (0.9 mm) lit. 64-65 0C (1.5 mm) Yield 5.3 g (59.5 percent) colorless liquid was obtained. 98percent (GC). 1H NMR: δ 3.56 and 3.23 (d-d and t, 2H, CH2-OH); 3.29 (m, IH, H2N-C*H) 1.8-2.4 (br, 3η, NH2 and OH) 1.68 (m, 1η, Cη2-CH(Cη3)2); 1.21 (t, 2H, C*H- CH2-CH); 0.89-0.94 (m, 6H, CH(CH3)2). 13C NMR: δ 67.12, 50.83, 43.68, 24.89, 23.58, 22.38.
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YieldReaction ConditionsOperation in experiment
73% at 0 - 20℃; for 17 h; General procedure: To a stirred and cooled to 0 °C, solution of l-leucine or l-iso-leucine (24.92 g, 0.189 mol) in 1.25 M H2SO4 (125 mL), a solution of sodium nitrite (19.73 g, 0.286 mol) in H2O (100 mL) was added dropwise. Next the mixture was stirred at 0 °C for 2 h and then at room temperature for 15 h. After this time, the contents of the flask were extracted with ethyl ether (6 .x. 75 mL). The organic layer was dried over MgSO4 and diethyl ether evaporated to yield the appropriate crude α-hydroxycarboxylic acid 2c or 2d, which was purified by recrystallization from hexane-ethyl ether mixture.
58% With sulfuric acid; sodium nitrite In water at 0 - 20℃; A solution of NaNO2 (6.3 g, 91.3 mmol) in water (20 ml) was added drop wise to an ice cooled and stirred solution of L- leucine (7.5 g, 57.2 mmol) in 1N H2SO4. The mixture was stirred for an additional 2 hour at 0-5 °C and left to stand overnight at room temperature. The resulting clear solution was concentrated in vacuum. The residual semi solid was extracted with ether and the organic layer was dried with Na2SO4. The solvent was removed in vacuum, and the residue was purified by column chromatography to give 4.4g (33.3 mmol, 58percent) of (S)-2-Hydroxy-4-methylpentanoic acid as colourless oil. [α]23D = -14.4 (c=1.00, CH3OH); 1H NMR (400 MHz,CD3OD) δ 4.16 (m, 1H), 1.85 (m, 1H), 1.58(m, 2H), 0.99(m, 6H); 13C NMR (100 MHz, CD3OD) δ178.5, 69.9, 44.5, 25.5, 23.7, 21.9.
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YieldReaction ConditionsOperation in experiment
88% With potassium carbonate In acetonitrile at 20℃; for 2 h; General procedure: To a solution of H-Phe-OH (100 mg, 60.5 mmol) in 50 percent MeCN (6.1 mL)were added Fmoc-OPhth (233 mg, 60.5 mmol) and K2CO3 (167 mg, 121 mmol) and stirred at room temperature. After 2 h of stirring saturated sodium bicarbonate solution and H2O were added and the resulting solution was washed with diethyl ether. The aqueous phase is acidified to pH 1 with 1M HCl and extracted with diethyl ether. The organic phase was washed with 1 M HCl, H2O, brine, dried over MgSO4. The filtrate was evaporatedevaporated under reduced pressure to give yellow solid as crude product.
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YieldReaction ConditionsOperation in experiment
100%
Stage #1: for 1 h; Cooling with ice
Stage #2: at 20 - 66℃; for 6.5 h;
Under ice bath, 100 ml round-bottom flask was added with 60 ml of methanol, and then slowly added with 4 ml of SOCl2 through constant pressure dropping funnel (with a drying tube on the top), and NaOH solution was used to absorb exhaust.
After stirring for 1 h, 8 mmol of L-leucine was added and stirred at room temperature for 30 min, and then refluxed at 66° C. for 6 h.
The reaction was tracked by TLC until the raw material disappears, with a solution of 2percent ninhydrin in ethanol as chromogenic reagent.
The solvent was evaporated out to obtain L-leucine methyl ester hydrochloride. Yield: 100percent.
96%
Stage #1: at -13 - -10℃; for 2 h;
Stage #2: at 50℃; for 3 h;
Take 115mL methanol, added to 250mL three-necked flask, Cool to -13 ° C in a low temperature stirred reaction bath (Reaction should ensure that the environment is anhydrous, In the three-necked flask branch pipe connected to the drying tube; The reaction generates HCl and SO2 gases, To use lye absorption device), Then 9.5 mL (0.131 mol) of freshly distilled SOCl2 was slowly added dropwise, When dropping the reaction temperature is controlled below -10° C , To be added dropwise after completion, continue to react at -10° C 2h, rise to room temperature, 15.4 g (0.118 mol) of leucine was added, and the temperature was raised to 50 ° C. for 3 hours, followed by TLC (With methanol and methylene chloride 1: 1 mixture as a developer, To prevent tailing, drop a drop of diethylamine per ml) Until the end of the reaction (about 3h) Stop the reaction. After the solvent was distilled off by rotary evaporation, A large amount of white solid appears. The product was purified by recrystallization from methanol to give pure leucine methyl ester hydrochloride in 96percent yield.
95% at -5 - 20℃; General procedure: A suspension of L-amino acid (50mmol) in methanol (50mL) was stirred under ice cold conditions. Thionyl chloride (5mL) was slowly dropped to the solution at−5°C. Then, the mixture was allowed to slowly warm to room temperature while being stirred. The reaction was monitored by TLC (N-butanol: water: acetic acid=4:1:1). When the reaction was completed, the solvent was evaporated under reduced pressure to afford the crude product, which was recrystallized from methanol/ether to give a white solid.
86% With thionyl chloride In methanol at -15 - 20℃; To a suspension of (L)-leucine, (315 g, 2.4 mol) in MeOH (3.2 L) at -15° C. was added SOCl2 (315 mL, 4.32 mol, 1.8 equiv.) dropwise at such a rate that the temp. of the reaction did not exceed 5° C. After the addition was complete, the reaction mixture was allowed to warm to room temp. and was stirred overnight. The resulting mixture was concentrated under reduced pressure and Et2O (3 L) was slowly added to the residue to produce a precipitate. The mixture was cooled with an ice bath, then treated with additional MeOH (3 L) relatively rapidly. After 1 h at 0° C., the crystals were collected and dried to give (L)-leucine methyl ester HCl salt as a white crystalline solid (394 g, 86percent): mp 147-149° C.; 1H-NMR (CD3OD) δ0.78-0.98 (m, 6 h), 1.58-1.72 (m, 3H), 3.76 (g, 3H), 3.92 (t, J=7.3 Hz, 1H)
72.2% at -17 - 20℃; for 18 h; To a suspension of l-leusine 26 (1.12 g, 8.54 mmol) in MeOH (9 mL)at -17 °C was slowly added thionylchloride (2.2 mL, 30.3 mmol) with stirring. Then, the mixture was brought tor.t. and stirred for further 18 h. The solution was concentrated in vacuo to give a white solid. The solid was re-crystalized to yield methylester hydrochloride salt 27 (1.12 g, 6.17 mmol72.2 percent).
56% at 20℃; Cooling with ice This compound has previously been described5 and can be purchased from Toronto Research. To a round bottom flask containing MeOH (50 mL) and cooled in an ice bath was added SOCl2 (6.1 mL, 84 mmol) dropwise over 5 min. L-Leucine 1e (5.0 g, 38) was then added and the mixture was left to stir overnight at rt. The reaction mixture was concentrated on the rotovap using MeOH (2 x 50 mL) to chase away excess thionyl chloride. Diethyl ether (50 mL) was added to the resulting solids and followed by a combination of scratching and sonication to produce a white solid which was filtered, rinsing with diethyl ether (3 x 10 mL). Product was further purified by recrystallization by partially dissolving solids in hot EtOAc (50 mL) followed by cooling to rt and filtration. Yield: 3.9 g (56percent). [α]D24 +18.8° (c 0.50, MeOH). >98percent pure by NMR. 1H NMR ((CD3)2SO) δ 8.61 (br s, 3H), 3.95 (t, J = 7, 1H), 3.74 (s, 3H), 1.75 (m, 1H), 1.65 (m, 2H), 0.89 (d, J = 7, 6H).

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YieldReaction ConditionsOperation in experiment
98% With thionyl chloride In methanol (1)
Similarly to Example 20 and starting from 6.56 g (50.0 mmol) of D,L-leucine, 50 ml of methanol and 13.0 ml (180 mmol) of thionyl chloride, 8.93 g (yield: 98percent) of D,L-leucine methyl ester hydrochloride was obtained as a white powder.
1H-NMR (300 MHz, D2O); δ: 4.17 (1H, t, J=6.8 Hz), 3.87 (3H, s), 1.90 (1H, m), 1.78 (2H, m), 00 (3H, d, J=6.0 Hz), 0.99 (3H, d, J=6.0 Hz).
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