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[ CAS No. 114676-59-4 ] {[proInfo.proName]}

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Chemical Structure| 114676-59-4
Chemical Structure| 114676-59-4
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Quality Control of [ 114676-59-4 ]

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Product Details of [ 114676-59-4 ]

CAS No. :114676-59-4 MDL No. :MFCD00082536
Formula : C6H12ClNO3 Boiling Point : -
Linear Structure Formula :- InChI Key :KLGSHNXEUZOKHH-TYSVMGFPSA-N
M.W : 181.62 Pubchem ID :12764090
Synonyms :
Chemical Name :(2R,4R)-Methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride

Calculated chemistry of [ 114676-59-4 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 11
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.83
Num. rotatable bonds : 2
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 44.97
TPSA : 58.56 ?2

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) : -7.24 cm/s

Lipophilicity

Log Po/w (iLOGP) : 0.0
Log Po/w (XLOGP3) : 0.24
Log Po/w (WLOGP) : -0.7
Log Po/w (MLOGP) : -0.5
Log Po/w (SILICOS-IT) : -0.25
Consensus Log Po/w : -0.24

Druglikeness

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

Water Solubility

Log S (ESOL) : -0.99
Solubility : 18.8 mg/ml ; 0.103 mol/l
Class : Very soluble
Log S (Ali) : -1.03
Solubility : 16.9 mg/ml ; 0.0933 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.06
Solubility : 159.0 mg/ml ; 0.873 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.51

Safety of [ 114676-59-4 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 114676-59-4 ]

* 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 [ 114676-59-4 ]

[ 114676-59-4 ] Synthesis Path-Downstream   1~5

  • 1
  • [ 24424-99-5 ]
  • [ 114676-59-4 ]
  • [ 114676-69-6 ]
YieldReaction ConditionsOperation in experiment
100% With dmap; triethylamine; In water; acetone; [0347] To a solution of <strong>[114676-59-4](2R,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride</strong> (4.4 g, 24.67 mmol) in Acetone and water (3:2, 30 mL) were added Et3N (6.8 mL , 49.28 mmol), DMAP (150 mg, 1.2 mmol). Then (Boc)20 (8.0 mL, 34.54 mmol) was added slowly and the reaction was stirred overnight. All the acetone was removed and diluted with EtOAc and washed with 0.5 N HC1, water, brine, dried and concentrated to yield 6.0 g of (2R,4R)-1- tert-butyl 2-methyl 4-hydroxypyrrolidine-l,2-dicarboxylate (quantitative).
93.4% At room temperature,(13.83 g, 76.38 mmol) was dissolved in a mixed solvent of 1,4-dioxane (50 mL) and water (20 mL), cooled to 0 ° C,Triethylamine (19.32 g, 190.95 mmol) was added and stirred for 10 min.Twenty-three butyl dicarbonate (21.67g, 99.29mmol)In dichloromethane (20 mL) was added dropwise to the reaction solution and reacted at room temperature overnight.Water (50 mL) was added to the reaction solution and extracted with dichloromethane (50 mL x 3).The organic phases were combined and washed with a hydrochloric acid solution (1 mol / L, 20 mL x 2) and a saturated aqueous saline solution (40 mL x 2).Dried over anhydrous magnesium sulfate, filtered, and the filtrate was concentrated under reduced pressure to give a pale yellow liquid 3C (17.49 g, yield 93.4percent).
88% With triethylamine; In dichloromethane; Step A-2. Preparation of a Boc compound To a suspension of <strong>[114676-59-4](2R,4R)-4-hydroxy-2-methoxycarbonylpyrrolidine hydrochloride</strong> (25.64 g: 125 mmole) in dichloromethane (125 ml), triethylamine (19.11 ml: 137.5 mmole) is added dropwise in a nitrogen atmosphere under ice cooling. The mixture is stirred for 5 minutes at room temperature. Then, a solution of di-t-butyl dicarbonate (34.11 g: 156.3 mmole) in dichloromethane (125 ml) is added dropwise, and the mixture is stirred for 40 minutes at room temperature to give (2R,4R)-1-t-butoxycarbonyl-4-hydroxy-2-methoxycarbonylpyrrolidine (26.85 g). Yield: 88percent. Colorless crystals. NMR delta(CDCl3) ppm: 1.46(d, J=8.4 Hz, 9H), 2.0 to 2.2(m, 1H), 2.2 to 2.5(m, 1H), 3.4 to 3.8(m, 2H), 3.79(d, J=3.0 Hz, 3H), 4.2 to 4.5(m, 2H). IR nu (KBr) cm-1: 3460, 1730, 1680.
88% Add triethylamine (265.9 g, 2.63 mol) to a solution of methyl ester hydrochloride in dry dichloromethane (2 L) at 0° C. and stir for 30 min. Then add N,N-dimethylaminopyridine (0.18 mol, 21.9 g) and di-tert-butyl dicarbonate (1.43 mol, 313.5 g) consecutively. Warm the reaction mixture to room temperature and stir for 18 h. Quench the reaction mixture with water, separate the organic layer and wash with water and NaHCO3 solution. Dry the organic layer over anhydrous sodium sulfate, filter, and concentrate under vacuum to obtain the title compound (260 g, 88percent) as a thick oil. 1H NMR (400 MHz, CDCl3) delta 1.43 (s, 9H), 1.46 (s, 9 H), 2.05-2.10 (m, 2H), 2.26-2.35 (m, 2H), 3.48-3.56 (m, 2H), 3.58-3.61 (m, 1H), 3.64-3.70 (m, 2H), 3.77 (s, 3H), 3.79 (s, 3H), 4.27-4.29 (m, 1H), 4.34-4.38 (m, 2H).
79% With N-ethyl-N,N-diisopropylamine; In 1,4-dioxane; at 0 - 20℃; for 1h; Add di-tert-butyl dicarbonate (10.4 g, 47.7 mmol) in 1,4-dioxane (10 mL) to a solution of 4- (R)-hydroxypyrrolidine-2-(R)-carboxylic methyl ester hydrochloride (6.66 g, 36.7 mmol) in 1,4-dioxane (80 mL). Cool in an ice bath and add N,N- diisopropylethylamine (11 mL, 62.4 mmol), then remove ice bath and stir 1 h at room temperature. Concentrate and dissolve in ethyl acetate and wash with aqueous citric acid solution (2 x 100 mL), water, saturated aqueous sodium bicarbonate, saturated aqueous sodium chloride, dry (magnesium sulfate), filter and concentrate to give the title compound as a white solid (7.1 g, 79percent). MS (ES): m/z = 246.1 [M+H].
77% With silica gel; triethylamine; In dichloromethane; at 23℃; for 5h; To a stirred suspension [OF 4R-HYDROXYPYRROLIDINE-2R-CARBOXYLIC] acid methyl ester hydrochloride salt (15.9 g, 76.3 mmol, 1 eq. ) in [CH2C12] (200 mL) at [23 °C] was added Et3N (21.3 mL, 153 mmol, 2 eq.) followed by Boc20 (21.1 mL, 91.6 mmol, 1.2 eq. ). The resulting mixture was stirred for 5 h, then treated with silica gel (20 g). The volatiles were removed in vacuo to give a free-flowing powder, which was dry-loaded onto a pre-packed silica gel column. The product was purified via flash column chromatography (100percent EtOAc as an eluent) to give [4R-HYDROXYPYRROLIDINE-1,] 2R-dicarboxylic acid [1-TERT-BUTYL] ester 2-methyl ester (14.4 g, 58.9 mmol, 77percent yield).

  • 2
  • [ 100-44-7 ]
  • [ 114676-59-4 ]
  • [ 114676-53-8 ]
  • 3
  • [ 67-56-1 ]
  • [ 2584-71-6 ]
  • [ 114676-59-4 ]
YieldReaction ConditionsOperation in experiment
100% With thionyl chloride; In methanol; at 0 - 23℃; for 16.025h; To a stirred solution [OF 4R-HYDROXYPYRROLIDINE-2R-CARBOXYLIC] acid (10.0 g, 76.3 mmol, [1] eq. ) in [MEOH] (300 mL) at [0 °C] was added SOC12 (10.0 mL, excess) over the course of 1.5 min. The reaction was allowed to warm to [23 °C.] After 16 h the reaction mixture was concentrated in vacuo to give 4R-hydroxypyrrolidine-2R-carboxylic acid methyl ester hydrochloride salt as a white solid (15.9 g, 100percent yield)
90% With thionyl chloride; at 0 - 20℃; for 72h; To a solution of (2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid 31.1 (1.0 eq) in MeOH (31 eq) at 0 °C was added S0C12 (1.2 eq) dropwise. The reaction solution was stirred at rt for 72 h. The resulting mixture was concentrated in vacuo to afford the compound 31.2 (90percent yield) as a white solid. LCMS (m/z): 146.0 [M+H] +. 1H NMR (400 MHz, DMSO-i/6) 3: 4.44 (d, J = 6.8 Hz, 1H), 4.33 (s, 1H), 3.70 (s, 3H), 3.03-3.00 (m, 1H), 2.30-2.23 (m, 1H), 2.14-2.09 (m, 1H), 1.17 (t, J = 7.2 Hz, 1H).
With acetyl chloride; for 8h;Inert atmosphere; Reflux; [0346] Acetyl chloride (2.45 mL, 34.53mmoles) was slowly added to MeOH (25mL) in a reaction flask under inert atmosphere. To this was added a solution of Cis-4-Hydroxy-D- proline (3.235g, 24.67 mmol) and refluxed for 8h. The reaction mixture was cooled to room temperature, and poured into ether (200mL). The precipitated solid was suction filtered and dried to yield (2R,4R)-methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride in quantitative yield. This was taken forward without purification.
  • 4
  • [ 75-36-5 ]
  • [ 2584-71-6 ]
  • [ 114676-59-4 ]
  • 5
  • [ 501-53-1 ]
  • [ 114676-59-4 ]
  • [ 155075-23-3 ]
YieldReaction ConditionsOperation in experiment
98% With sodium hydrogencarbonate; In 1,4-dioxane; water; at 0℃; for 2.5h; A solution of (2S, 4R) -methyl 4-hydroxypyrrolidine-2-carboxylate hydrochloride (5.5 g, 30 mmol) in 1, 4-dioxane (17 mL) was cooled to 0 , and then a solution of sodium carbonate (3.5 g, 33 mmol) in H 2O (17 mL) was added in portions, after that, CbzCl (4.8 mL, 34 mmol) was added over 30 min. The obtaining reaction mixture was stirred at 0 for 2 hours. The mixture was concentrated in vacuo to remove 1, 4-dioxane, the residue was extracted with ethyl acetate (3 x 100 mL) . The combined organic phases were dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated in vacuo. The residue was purified by silica gel chromatograph (PE/EtOAc (V/V) = 1/1) to give the title compound as a colorless oil (6.7 g, 79%) .
98% With sodium hydrogencarbonate; In 1,4-dioxane; water; at 0℃; for 2.5h; <strong>[114676-59-4](2R,4R)-4-hydroxypyrrolidine-2-carboxylic acid methyl ester hydrochloride</strong> (8 g, 44.0 mmol), 1,4-dioxane(80mL), water (80mL),Sodium bicarbonate (7.4 g, 88 mmol) andBenzyl chloroformate (8.0 mL, 53 mmol) was used as a raw material.According to the method of step 1 of embodiment 1,The title compound was obtained as a colorless oil (12.1 g, yield: 98%).(2S,4R)-4-Hydroxypyrrole-2-carboxylic acid methyl ester hydrochloride (5.5 g, 30 mmol) The 1,4-dioxane (17 mL) solution was cooled to 0 C. Then sodium carbonate (3.5 g, 33 mmol) was added in portions. H2O (17mL) solution, Then add CbzCl (4.8 mL, 34 mmol), After 30 minutes, the drop is completed. The resulting reaction solution was stirred at 0 C for 2 hours. The reaction mixture was concentrated to dryness The residue was purified with EtOAc EtOAc m. The title compound was obtained as a colorless oil ( 6.7 g, yield: 79%).
7.4 g With sodium carbonate; In tetrahydrofuran; water; at 0 - 20℃; for 2h; To a solution of D (17.94 g, 98.8 mmol) and Na2C03 (10.5 g, 98.8 mmol) in THF/H20 (150 mL/50 mL) was added CbzCI (20.2 g, 1 18.56 mmol) at 0 C and the mixture was stirred at room temperature for 2 h. The mixture was filtered through filter paper and the filtrate was concentrated. Water (200 mL) was added and the product was extracted with EtOAc (100 ml x 3). The combined organic layers were washed with brine, dried (MgS0 ), filtered, and concentrated. The residue was purified by column chromatography (silica gel, PetEther/EtOAc=5/1 -2/1) to get the desired product (7.4 g, 27%) as a light yellow oil. LC-MS : 279.9 ([M+1]+ ).
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