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[ CAS No. 51293-47-1 ] {[proInfo.proName]}

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Chemical Structure| 51293-47-1
Chemical Structure| 51293-47-1
Structure of 51293-47-1 * Storage: {[proInfo.prStorage]}
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Product Details of [ 51293-47-1 ]

CAS No. :51293-47-1 MDL No. :MFCD00153314
Formula : C9H17NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :-
M.W : 219.24 Pubchem ID :-
Synonyms :

Calculated chemistry of [ 51293-47-1 ]

Physicochemical Properties

Num. heavy atoms : 15
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.78
Num. rotatable bonds : 7
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 52.75
TPSA : 84.86 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) : -7.35 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.76
Log Po/w (XLOGP3) : 0.41
Log Po/w (WLOGP) : 0.61
Log Po/w (MLOGP) : 0.01
Log Po/w (SILICOS-IT) : -0.14
Consensus Log Po/w : 0.53

Druglikeness

Lipinski : 0.0
Ghose : None
Veber : 0.0
Egan : 0.0
Muegge : 0.0
Bioavailability Score : 0.56

Water Solubility

Log S (ESOL) : -1.0
Solubility : 22.1 mg/ml ; 0.101 mol/l
Class : Very soluble
Log S (Ali) : -1.76
Solubility : 3.82 mg/ml ; 0.0174 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.79
Solubility : 35.2 mg/ml ; 0.161 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.97

Safety of [ 51293-47-1 ]

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 [ 51293-47-1 ]

* 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 [ 51293-47-1 ]
  • Downstream synthetic route of [ 51293-47-1 ]

[ 51293-47-1 ] Synthesis Path-Upstream   1~9

  • 1
  • [ 4219-94-7 ]
  • [ 24424-99-5 ]
  • [ 51293-47-1 ]
YieldReaction ConditionsOperation in experiment
98% With sodium hydroxide In tetrahydrofuran; water at 0 - 20℃; To 2.0 g (17 mmol) of C606-1 were added 35 ml of a IN aqueous sodium hydroxide solution and 35 ml of THF. A solution of di-tert- butyl dicarbonate (4.03 g, 18.5 mmol) in THF (15 mL) was then added with stirring at 0°C. The reaction mixture was stirred overnight at room temperature and concentrated by evaporation under reduced pressure. The aqueous phase was acidified to pH 4-5 with 10percent aqueous citric acid and extracted with ethyl acetate. The extract was washed with brine, dried (MgS04), and evaporated to give 3.6 g of compound 606-2 (98 percent yield). MS (ESI) m/z: 220.1 (M+H)+.
Reference: [1] Chemistry - A European Journal, 2011, vol. 17, # 15, p. 4183 - 4194
[2] Patent: WO2016/11088, 2016, A2, . Location in patent: Paragraph 00238; 00239
  • 2
  • [ 3262-72-4 ]
  • [ 74-88-4 ]
  • [ 51293-47-1 ]
YieldReaction ConditionsOperation in experiment
28%
Stage #1: With methanol; sodium hydride In tetrahydrofuran; mineral oil at 20℃; for 1 h;
Stage #2: at 20℃; for 38 h;
Stage #3: With citric acid In water
A. (S)-2-(tert-Butoxycarbonylamino)-3-methoxypropanoic acid A sodium methanolate (NaOMe) solution was prepared by slowly adding MeOH (50 mL) to a suspension of sodium hydride (60percent in mineral oil, 28 g, 0.71 mol) in dry THF (1.2 L) at 0° C. The resulting mixture was stirred at RT for 2 h. A portion of the NaOMe solution (320 mL) was added to (S)-2-(tert-butoxycarbonylamino)-3-hydroxypropanoic acid (36 g, 175 mmol) in dry THF (1.6 L), and the mixture was stirred at RT for 1 h. Methyl iodine (16 mL) was then added and the mixture was stirred at RT for 1 h. Another aliquot of NaOMe solution (540 mL) was added and the reaction mixture stirred at RT for 1 h. Additional methyl iodine (38 mL) in THF (200 mL) was added and the reaction mixture was stirred at RT for 36 h. Following reaction, the mixture was concentrated and the residue was dissolved in water and washed with diethyl ether (2.x.100 mL). The aqueous layer was acidified to pH 2 by the addition of solid citric acid and was extracted with EtOAc (3.x.200 mL) and dried over Na2SO4. The organic phase was concentrated, and the residue was dissolved in water and extracted with DCM (4.x.150 mL). The organic layers were combined and concentrated to give the title compound as an oil, which was used without further purification (10.9 g, 28percent).
Reference: [1] Patent: US2011/152273, 2011, A1, . Location in patent: Page/Page column 87
[2] Journal of Organic Chemistry, 1979, vol. 44, p. 2299 - 2300
  • 3
  • [ 183793-47-7 ]
  • [ 51293-47-1 ]
Reference: [1] Journal of Organic Chemistry, 1996, vol. 61, # 22, p. 7671 - 7676
  • 4
  • [ 69912-63-6 ]
  • [ 51293-47-1 ]
Reference: [1] Patent: WO2005/75439, 2005, A1, . Location in patent: Page/Page column 119; 125
[2] Patent: US2005/203078, 2005, A1, . Location in patent: Page/Page column 62
  • 5
  • [ 75-18-3 ]
  • [ 3262-72-4 ]
  • [ 51293-47-1 ]
YieldReaction ConditionsOperation in experiment
240.3 kg at 10℃; for 44 h; Large scale Example 2 Synthesis of (S)-2-((tert-butoxycarbonyl)amino)-3-methoxypropanoic acid (0033) (0034) 45percent 4 NaOH (746.3 kg; 8.40 kmoles) and DMS (1053.8 kg; 8.36 kmoles) were added to the reaction mixture below 10° C. over 38 h and for an additional 6 h to complete the reaction. 20percent 9 NH4OH (20.0 kg) was added to quench the reaction in the reaction mixture. The pH value was adjusted by 10 citric acid monohydrate (55.8 kg) and 32percent 11 HCl (180 kg) to around 3. The 12 product was extracted by toluene (1165 L) twice, and the organic layer was washed by 1percent NaOH (40 L) and H2O (39 L×2). The organic layer was concentrated, and stripped by IPA as oil residue (240.3 kg)
Reference: [1] Patent: US9718765, 2017, B1, . Location in patent: Page/Page column 5; 6
  • 6
  • [ 134167-07-0 ]
  • [ 51293-47-1 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 1, p. 67 - 70
  • 7
  • [ 24424-99-5 ]
  • [ 51293-47-1 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 1, p. 67 - 70
  • 8
  • [ 2766-43-0 ]
  • [ 51293-47-1 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 1, p. 67 - 70
  • 9
  • [ 1070-19-5 ]
  • [ 51293-47-1 ]
Reference: [1] Journal of Organic Chemistry, 1974, vol. 39, p. 1870 - 1872
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