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[ CAS No. 94885-52-6 ] {[proInfo.proName]}

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Cat. No.: {[proInfo.prAm]}
Chemical Structure| 94885-52-6
Chemical Structure| 94885-52-6
Structure of 94885-52-6 * Storage: {[proInfo.prStorage]}
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Product Details of [ 94885-52-6 ]

CAS No. :94885-52-6 MDL No. :MFCD14635629
Formula : C12H13NO3 Boiling Point : -
Linear Structure Formula :- InChI Key :NVKOCDGGRHAHOJ-JTQLQIEISA-N
M.W :219.24 Pubchem ID :2381219
Synonyms :

Calculated chemistry of [ 94885-52-6 ]

Physicochemical Properties

Num. heavy atoms : 16
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 4
Num. H-bond acceptors : 3.0
Num. H-bond donors : 1.0
Molar Refractivity : 61.53
TPSA : 55.4 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) : -6.88 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.07
Log Po/w (XLOGP3) : 1.06
Log Po/w (WLOGP) : 0.48
Log Po/w (MLOGP) : 1.06
Log Po/w (SILICOS-IT) : 1.88
Consensus Log Po/w : 1.31

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.88
Solubility : 2.89 mg/ml ; 0.0132 mol/l
Class : Very soluble
Log S (Ali) : -1.81
Solubility : 3.36 mg/ml ; 0.0153 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -3.32
Solubility : 0.106 mg/ml ; 0.000482 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.31

Safety of [ 94885-52-6 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 UN#:N/A
Hazard Statements:H302-H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 94885-52-6 ]

* 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 [ 94885-52-6 ]
  • Downstream synthetic route of [ 94885-52-6 ]

[ 94885-52-6 ] Synthesis Path-Upstream   1~5

  • 1
  • [ 94885-52-6 ]
  • [ 91229-91-3 ]
Reference: [1] Tetrahedron, 2004, vol. 60, # 45, p. 10277 - 10284
[2] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 6, p. 507 - 514
[3] Tetrahedron Letters, 1992, vol. 33, # 32, p. 4617 - 4620
  • 2
  • [ 24424-99-5 ]
  • [ 94885-52-6 ]
  • [ 113400-36-5 ]
YieldReaction ConditionsOperation in experiment
73.8% With dmap In dichloromethane at 0 - 20℃; D-1 (8 g, 36.5 mmol, 1 eq) was dissolved in DCM (150 mL). The mixture was stirred and was cooled to 0° C. Dimethylaminopyridine (DMAP, 4.9 g, 40.1 mmol, 1.1 eq) was added followed by Boc-anhydride ((BOC)2O, 8.75 g, 40.1 mmol, 1.1 eq). The mixture was allowed to warm to room temperature and was stirred for 2 hours. The mixture was then diluted with DCM (250 mL) and was washed successively with aqueous HCl (1N, 50 mL), aqueous saturated bicarbonate solution (350 mL) and brine. The organic phase was dried over sodium sulfate, was concentrated under reduced pressure, and was purified by silica gel chromatography to provide D-2 (8.6 g, 73.8percent). LCMS (ES+, m/e=656, [2M+NH4+]).
51.2 g With dmap; triethylamine In dichloromethane at 20℃; for 16 h; Cooling with ice Benzyl chloride (25.3ml, 0.22mol) was added to a solution of 5-oxo-l-proline (2) (25.8g, 0.20mol) with triethylamine (28.0ml, 0.20mol) in THF (260ml). The reaction mixture was refluxed at 70°C for 5days. After cooling the mixture to room temperature, the solvent was removed in vacuo. The residue was diluted with water, and extracted with chloroform. The organic layer was washed with brine, and dried over magnesium sulfate. The mixture was filtered, and the solvent was removed in vacuo to afford the crude product as pale brown oil. To a stirred solution of the product in dichloromethane (400ml) was added di-tert-butyl dicarbonate (44g, 0.20mol), triethylamine (28ml, 0.2mol) and DMAP (12.2g, 0.10mol) under an ice cooling bath. The solution was warmed to room temperature and stirred for 16h. The reaction mixture was diluted with water, and extracted with chloroform. The organic layer was washed with brine, and dried over magnesium sulfate. The mixture was filtered, and the solvent was removed in vacuo to afford crude product. The residue was purified by flash silica gel chromatography withn-hexane/EtOAc (2:1, v/v) to give the colorless solid (51.2g, 80percent yield);1H NMR (400MHz, CDCl3)δ: 1.42 (9H, s), 1.98–2.05 (1H, m), 2.26–2.37 (1H, m), 2.44–2.51 (1H, m), 2.57–2.66 (1H, m), 4.64 (1H, dd,J=9.5, 2.9Hz), 5.19 (1H, d,J=12.0Hz), 5.23 (1H, d,J=12.2Hz), 7.34–7.37 (5H, m); ESI/MS:m/z=342 (M+Na).
Reference: [1] Tetrahedron Letters, 2002, vol. 43, # 19, p. 3499 - 3501
[2] Chemistry (Weinheim an der Bergstrasse, Germany), 2002, vol. 8, # 11, p. 2516 - 2525
[3] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 6, p. 507 - 514
[4] Tetrahedron, 2004, vol. 60, # 45, p. 10277 - 10284
[5] Patent: US2014/248242, 2014, A1, . Location in patent: Paragraph 0402; 0404
[6] Tetrahedron Letters, 1992, vol. 33, # 32, p. 4617 - 4620
[7] Synthetic Communications, 1995, vol. 25, # 24, p. 4045 - 4052
[8] Tetrahedron, 1998, vol. 54, # 9, p. 1753 - 1762
[9] Organic Letters, 2004, vol. 6, # 9, p. 1469 - 1471
[10] Journal of Organic Chemistry, 2000, vol. 65, # 7, p. 2163 - 2171
[11] Journal of the American Chemical Society, 2001, vol. 123, # 39, p. 9706 - 9707
[12] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 10, p. 3474 - 3488
[13] Patent: US6277851, 2001, B1,
[14] Journal of Medicinal Chemistry, 2010, vol. 53, # 18, p. 6572 - 6583
[15] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 14, p. 4319 - 4331
[16] Journal of the American Chemical Society, 2015, vol. 137, # 7, p. 2776 - 2784
  • 3
  • [ 34619-03-9 ]
  • [ 94885-52-6 ]
  • [ 113400-36-5 ]
Reference: [1] Patent: WO2006/24501, 2006, A1, . Location in patent: Page/Page column 41
  • 4
  • [ 94885-52-6 ]
  • [ 53100-44-0 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2007, vol. 15, # 10, p. 3474 - 3488
[2] Chemistry (Weinheim an der Bergstrasse, Germany), 2002, vol. 8, # 11, p. 2516 - 2525
[3] Journal of the Chemical Society - Perkin Transactions 1, 1996, # 6, p. 507 - 514
  • 5
  • [ 94885-52-6 ]
  • [ 334769-80-1 ]
Reference: [1] Bioorganic and Medicinal Chemistry, 2013, vol. 21, # 14, p. 4319 - 4331
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