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[ CAS No. 155075-23-3 ] {[proInfo.proName]}

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Chemical Structure| 155075-23-3
Chemical Structure| 155075-23-3
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Product Details of [ 155075-23-3 ]

CAS No. :155075-23-3 MDL No. :MFCD09954933
Formula : C14H17NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :VVKAGQHUUDRPOI-VXGBXAGGSA-N
M.W : 279.29 Pubchem ID :688410
Synonyms :
Chemical Name :1-Benzyl 2-methyl (2R,4R)-4-hydroxypyrrolidine-1,2-dicarboxylate

Calculated chemistry of [ 155075-23-3 ]      Expand+

Physicochemical Properties

Num. heavy atoms : 20
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.43
Num. rotatable bonds : 6
Num. H-bond acceptors : 5.0
Num. H-bond donors : 1.0
Molar Refractivity : 73.87
TPSA : 76.07 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) : -7.23 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.37
Log Po/w (XLOGP3) : 1.09
Log Po/w (WLOGP) : 0.4
Log Po/w (MLOGP) : 0.76
Log Po/w (SILICOS-IT) : 0.66
Consensus Log Po/w : 1.06

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.08
Solubility : 2.3 mg/ml ; 0.00824 mol/l
Class : Soluble
Log S (Ali) : -2.28
Solubility : 1.47 mg/ml ; 0.00525 mol/l
Class : Soluble
Log S (SILICOS-IT) : -1.98
Solubility : 2.96 mg/ml ; 0.0106 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 0.0
Synthetic accessibility : 3.33

Safety of [ 155075-23-3 ]

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 [ 155075-23-3 ]

* 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 [ 155075-23-3 ]
  • Downstream synthetic route of [ 155075-23-3 ]

[ 155075-23-3 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 2584-71-6 ]
  • [ 155075-23-3 ]
YieldReaction ConditionsOperation in experiment
100% With sodium hydrogencarbonate In water; toluene at 23℃; for 24.25 h; To a stirred solution of 4R-hydroxypyrrolidine-2R-carboxylic acid (5.02 g, 38.3 mmol, 1 eq. ) and [NAHC03] (8.05 g, 95.8 mmol, 2.5 eq. ) in H20 (85 mL) at 23 [°C] was added a solution of Cbz-Cl (6.28 mL, 44.0 mmol, 1.15 eq. ) in toluene (20 mL) over 15 min period. After 24 h the layers were separated and the aqueous layer was extracted with Et2O (2 x 100 mL) and discarded the combined organic layer. The aqueous layer was then acidified to pH 2 with concentrated [HCI,] and the product was extracted with EtOAc (2 x 100 mL). The organic layer was dried and concentrated in vacuo to give [4R-HYDROXYPYRROLIDINE-1,] [2R-DICARBOXYLIC] acid [1-] benzyl ester 2-methyl ester (9.97 g, [100percent)
Reference: [1] Patent: WO2004/7444, 2004, A2, . Location in patent: Page 139
[2] Collection of Czechoslovak Chemical Communications, 1996, vol. 61, p. S234 - S237
[3] Journal of the American Chemical Society, 1996, vol. 118, # 29, p. 6826 - 6840
[4] Patent: WO2016/11930, 2016, A1,
  • 2
  • [ 130930-25-5 ]
  • [ 74-88-4 ]
  • [ 155075-23-3 ]
YieldReaction ConditionsOperation in experiment
89% With sodium hydrogencarbonate In N,N-dimethyl-formamide at 50℃; The (2R,4R)-1 -((benzyl oxy)carbonyl)-4-hydroxypyrrolidine -2 -carboxylic acid(2.02 g, 7.63 mmol) and NaHCO3 (1.28 g, 15.3 mmol) were suspended in DMF (10 ml). Methyl iodide (2.37 ml, 5.41 g, 38.13 mmol) was added to the mixture, which was then stirred and heated at 500C overnight. After concentrating the reaction under reduced pressure, the residue was partitioned between ethyl acetate and water. The aqueous layer was extracted once more with ethyl acetate, and the combined organic layers were washed with brine, dried (MgSO4) and concentrated. The residue was purified by silica flash <n="128"/>chromatography (gradient elution, using 1 : 1 hexane-ethyl acetate and ethyl acetate) to provide the title compound as a colorless oil (1.9 g, 89percent).
Reference: [1] Patent: WO2008/24725, 2008, A1, . Location in patent: Page/Page column 126-127
[2] Patent: WO2016/11930, 2016, A1, . Location in patent: Page/Page column 120
[3] Patent: WO2009/137130, 2009, A2, . Location in patent: Page/Page column 52-53
  • 3
  • [ 501-53-1 ]
  • [ 155075-23-3 ]
YieldReaction ConditionsOperation in experiment
69% With N-ethyl-N,N-diisopropylamine In dichloromethane at 0℃; for 0.5 h; A solution of cis-hydroxy-D-proline (2.98 g, 22.7 mmol) in methanol (20 mL) was treated with thionyl chloride (1.78 mL, 24.4 mmol) and stirred at room temperature for 1 h. The reaction mixture was then heated to 65 °C overnight. Evaporation of the volatiles gave the crude methyl ester (4.0816 g), which was dissolved in dichloromethane (50 mL) and diisopropyl ethyl amine (9.59 mL, 55.1 mmol) was added. The reaction mixture was cooled to 0 °C and neat benzyl chloroformate (3.71 mL, 26.0 mmol) was added via syringe. After stirring at 0 °C for 30 minutes the cooling bath was removed. The reaction was quenched by pouring into an aqueous solution of citric acid (10 percent, 50 mL) and the product was extracted into dichloromethane. The combined organic phases were back-washed with brine, dried with anhydrous sodium sulfate, and the solvent was removed in vacuo. The crude product was purified by flash chromatography (silica gel, ethyl acetate: hexanes/4: 6) to yield 4.0717 g (69 percent) of the pure PRODUCT. H NMR (500 MHz, CDCL3) : 8 7. 35 M (5H), 5.21 (d, J = 12. 6 HZ, 2H), 5.10 (d, J = 13 Hz, 1H), 5.06 (d, J = 12.35 Hz, 1H), 4.45 (m, 2H), 3.80 (s, 3H), 2.35 (m, 1H), 2.15 (m, 1H).
Reference: [1] Patent: WO2004/94371, 2004, A2, . Location in patent: Page 127-128
  • 4
  • [ 501-53-1 ]
  • [ 114676-59-4 ]
  • [ 155075-23-3 ]
YieldReaction ConditionsOperation in experiment
7.4 g With sodium carbonate In tetrahydrofuran; water at 0 - 20℃; for 2 h; 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, 27percent) as a light yellow oil. LC-MS : 279.9 ([M+1]+ ).
Reference: [1] Journal of the American Chemical Society, 1996, vol. 118, # 29, p. 6826 - 6840
[2] Patent: WO2014/32, 2014, A1, . Location in patent: Page/Page column 64; 65
  • 5
  • [ 501-53-1 ]
  • [ 114676-47-0 ]
  • [ 155075-23-3 ]
Reference: [1] Patent: US2008/81803, 2008, A1, . Location in patent: Page/Page column 64
  • 6
  • [ 7732-18-5 ]
  • [ 584-08-7 ]
  • [ 501-53-1 ]
  • [ 2584-71-6 ]
  • [ 155075-23-3 ]
Reference: [1] Patent: US5436229, 1995, A,
  • 7
  • [ 7732-18-5 ]
  • [ 584-08-7 ]
  • [ 501-53-1 ]
  • [ 2584-71-6 ]
  • [ 155075-23-3 ]
Reference: [1] Patent: US5578574, 1996, A,
  • 8
  • [ 186581-53-3 ]
  • [ 130930-25-5 ]
  • [ 155075-23-3 ]
Reference: [1] Tetrahedron, 2009, vol. 65, # 4, p. 862 - 876
[2] Collection of Czechoslovak Chemical Communications, 1996, vol. 61, p. S234 - S237
[3] Chemistry - A European Journal, 1997, vol. 3, # 12, p. 1997 - 2010
  • 9
  • [ 130930-25-5 ]
  • [ 18107-18-1 ]
  • [ 155075-23-3 ]
Reference: [1] Bioorganic and Medicinal Chemistry Letters, 2013, vol. 23, # 16, p. 4608 - 4616
  • 10
  • [ 444313-67-1 ]
  • [ 155075-23-3 ]
Reference: [1] Patent: WO2014/32, 2014, A1,
  • 11
  • [ 77449-94-6 ]
  • [ 155075-23-3 ]
Reference: [1] Patent: WO2014/32, 2014, A1,
  • 12
  • [ 51-35-4 ]
  • [ 155075-23-3 ]
Reference: [1] Patent: WO2014/32, 2014, A1,
  • 13
  • [ 501-53-1 ]
  • [ 155075-23-3 ]
Reference: [1] Patent: WO2016/11930, 2016, A1,
  • 14
  • [ 75315-63-8 ]
  • [ 114676-59-4 ]
  • [ 155075-23-3 ]
Reference: [1] Chemistry - A European Journal, 2010, vol. 16, # 35, p. 10691 - 10706
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