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[ CAS No. 57224-63-2 ] {[proInfo.proName]}

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Chemical Structure| 57224-63-2
Chemical Structure| 57224-63-2
Structure of 57224-63-2 * Storage: {[proInfo.prStorage]}
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Product Details of [ 57224-63-2 ]

CAS No. :57224-63-2 MDL No. :MFCD00038585
Formula : C13H17NO5 Boiling Point : -
Linear Structure Formula :- InChI Key :OPZWAOJFQFYYIX-KOLCDFICSA-N
M.W : 267.28 Pubchem ID :2733409
Synonyms :

Calculated chemistry of [ 57224-63-2 ]

Physicochemical Properties

Num. heavy atoms : 19
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.38
Num. rotatable bonds : 8
Num. H-bond acceptors : 5.0
Num. H-bond donors : 2.0
Molar Refractivity : 67.17
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) : -7.12 cm/s

Lipophilicity

Log Po/w (iLOGP) : 1.87
Log Po/w (XLOGP3) : 1.14
Log Po/w (WLOGP) : 0.68
Log Po/w (MLOGP) : 0.89
Log Po/w (SILICOS-IT) : 0.95
Consensus Log Po/w : 1.11

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.92
Solubility : 3.21 mg/ml ; 0.012 mol/l
Class : Very soluble
Log S (Ali) : -2.52
Solubility : 0.814 mg/ml ; 0.00305 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.53
Solubility : 0.789 mg/ml ; 0.00295 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 3.21

Safety of [ 57224-63-2 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P280-P305+P351+P338 UN#:N/A
Hazard Statements:H302 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 57224-63-2 ]

* 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 [ 57224-63-2 ]
  • Downstream synthetic route of [ 57224-63-2 ]

[ 57224-63-2 ] Synthesis Path-Upstream   1~14

  • 1
  • [ 39994-75-7 ]
  • [ 501-53-1 ]
  • [ 57224-63-2 ]
YieldReaction ConditionsOperation in experiment
89.1% With sodium hydrogencarbonate; sodium hydroxide In water The In a 2L beaker, 100 g of L-threonine methyl ester hydrochloride, 600 ml of water and adjusted to pH of sodium bicarbonate were added dropwise, and z-cl 110 g was added dropwise and the pH was adjusted with 2 moc / l sodium hydroxide 8-9 reaction. The reaction was terminated, 1L of ethyl acetate was added, 500ML washed with water, washed with 500ml of saturated brine, dried over 100g of anhydrous sodium sulfate, filtered and evaporated to a solid solution under reduced pressure. The granite was crystallized at 600Ml, filtered and dried to obtain z-thr-ome 140 g, yield 89.1percent;
Reference: [1] Patent: CN106631900, 2017, A, . Location in patent: Paragraph 0015
[2] Journal of the Chemical Society - Perkin Transactions 1, 1999, # 24, p. 3697 - 3703
[3] Justus Liebigs Annalen der Chemie, 1962, vol. 656, p. 190 - 204
[4] Journal of Organic Chemistry, 1985, vol. 50, # 23, p. 4515 - 4523
[5] Patent: WO2010/17060, 2010, A1, . Location in patent: Page/Page column 44-45
  • 2
  • [ 19728-63-3 ]
  • [ 74-88-4 ]
  • [ 57224-63-2 ]
YieldReaction ConditionsOperation in experiment
92% With potassium carbonate In N,N-dimethyl-formamide at 20℃; for 3 h; General procedure: A solution of N-benzyloxycarbonyl-L-amino acid S5 (7.9 mmol) in DMF (20 ml) was added methyliodide (1.1 g, 7.9 mmol) and potassium carbonate (1.2 g, 8.7 mmol). The reaction mixture waskept at room temperature for 3 hours. The methylated products were purified by column chromatographyin the yields of 50percent (1.0 g, colorless-oil) for serine and 92percent (1.9 g, white-solid) for threonine.The methylated amino acid (4.0 mmol) in DMF (10 ml) was mixed with TBDPSCl (2.2 g, 7.9mmol), imidazole (810 mg, 11.9 mmol) and catalytic amount of DMAP. The reaction was processedat 45 °C for 7 hours. The desired products were purified by column chromatography in theyields of 90percent (1.7 g, colorless-oil) for serine and 90percent (1.8 g, white-solid) for threonine. The silylproduct (500 mg, 1.0 mmol) in DMF (1 ml) was reacted with 15percent NaOH (5 ml) for 2 hours. Thereaction mixture was quenching by 1 N HCl(aq) and 6 was extracted by ethyl acetate. The desiredamino acid 6 was obtained after removal of ethyl acetate in the quantitative yields (470 mg,white-solid for serine; 486 mg, colorless-oil for threonine).
Reference: [1] Synlett, 2018, vol. 29, # 11, p. 1430 - 1436
  • 3
  • [ 3373-59-9 ]
  • [ 501-53-1 ]
  • [ 57224-63-2 ]
YieldReaction ConditionsOperation in experiment
70 g With sodium hydrogencarbonate In 1,4-dioxane; water at 0 - 20℃; for 13 h; [00283] To a stirring solution of 6S-X (60 g, 353 mmol) in water/1,4 dioxane (150 m l. 300 ml.) The reaction mixture was cooled to 0 CC added NaHCO -, (88.9 g, 1.059 mol) at 0 C and stirred for 15 min.. Cbz-CI (60.7 mL, 426 mmol) was added drop wise and stirred for 1h. The reaction mixture was stirred to RT and stirred for 12 h. After completion of starting material (by TLC), diluted the reaction mass with EtOAc (300 ml). The separated organic layer was washed with (2x200 ml. ) of saturated aHCO * solution followed by brine solution (2x100 mL ). The organic layer was dried over anhydrous Na2S04, filtered and concentrated under reduced pressure to afford crude material was triturated with -hexane (500mL) to afford 6S-Y (70 g, 74 percent) as white solid. H-NMR: (400 MHz, DMSO-d6): δ 7.37-7.30 (m, 5H), 7.20 (d, J = 8.4 Hz, 1H), 5.06 (s, 2H), 4.78 (d, J= 6.8 Hz, 1H), 4.09-4.05 (m, 2H), 3.64 (s, 3H), 1.09 (d, J= 6.0 Hz, 3H). LCMS m/z: 268.2[M++1]
70 g
Stage #1: With sodium hydrogencarbonate In 1,4-dioxane; water at 0℃; for 0.25 h;
Stage #2: at 0 - 20℃; for 13 h;
To a stirring solution of 4S-H (60 g, 353 mmol) in water/1,4 dioxane (150 mL/300 mL) The reaction mixture was cooled to 0 °C added NaHCO3 (88.9 g, 1.059 mol) at 0 C and stirred for 1 min. Cbz-Cl (60.7 mL. 426 mmol) was added drop wise and stirred for 1 h. The reaction mixture was stirred to RT and stirred for 12 h. After completion of starting material (by TLC), diluted the reaction mass with EtOAc (300 ml). The separated organic layer was washed with (2x200 mL) of saturated NaHCO3 solution followed by brine solution (2x100 mL). The organic layer was dried over anhydrous Na2SO4, filtered and concentrated under reduced pressure to afford crude material was triturated with n-hexane (500mL) to afford 4S-I (70 g, 74 percent) as white solid. 1H-NMR: (400 MHz, DMSO-d6): δ 7.37-7.30 (m, 5H), 7.20 (d, J = 8.4 Hz, 1H), 5.06 (s, 2H), 4.78 (d, J= 6.8 Hz, 1H), 4.09-4.05 (m, 2H), 3.64 (s, 3H), 1.09 (d, J= 6.0 Hz, 3H). LCMS m/z: 268.2[M++1]
105 kg With sodium carbonate In methanolLarge scale Plus 99. 5percent of the 125 kg of methanol,A saturated solution of sodium carbonate was added dropwise,Adjusting the pH of the solution to 7-8;50 kg of benzyl chloroformate was added dropwise,Reaction 3-5h, filtration,To give 105 kg of β-hydroxy N-formyl benzyl ester threonine methyl ester
Reference: [1] Patent: WO2014/120800, 2014, A1, . Location in patent: Paragraph 00283; page 177
[2] Patent: WO2014/120786, 2014, A1, . Location in patent: Paragraph 0107
[3] Patent: CN102285907, 2016, B, . Location in patent: Paragraph 0030; 0031
  • 4
  • [ 67-56-1 ]
  • [ 19728-63-3 ]
  • [ 57224-63-2 ]
Reference: [1] Journal of the American Chemical Society, 1987, vol. 109, # 17, p. 5167 - 5175
[2] Tetrahedron, 2000, vol. 56, # 29, p. 5077 - 5083
[3] Organic Letters, 2005, vol. 7, # 22, p. 5047 - 5050
[4] Tetrahedron, 2007, vol. 63, # 35, p. 8645 - 8657
[5] Chemical Communications, 2014, vol. 50, # 88, p. 13608 - 13611
[6] Canadian Journal of Chemistry, 1962, vol. 40, p. 2229 - 2233
[7] Bulletin of the Chemical Society of Japan, 1978, vol. 51, # 6, p. 1897 - 1898
[8] Organic Letters, 2010, vol. 12, # 7, p. 1624 - 1627
[9] Journal of the American Chemical Society, 2011, vol. 133, # 1, p. 102 - 107
  • 5
  • [ 863650-79-7 ]
  • [ 57224-63-2 ]
Reference: [1] Journal of Organic Chemistry, 2008, vol. 73, # 2, p. 752 - 755
  • 6
  • [ 245115-65-5 ]
  • [ 57224-63-2 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 4, p. 1037 - 1049
  • 7
  • [ 186581-53-3 ]
  • [ 19728-63-3 ]
  • [ 57224-63-2 ]
Reference: [1] Tetrahedron, 1987, vol. 43, # 22, p. 5341 - 5349
[2] Justus Liebigs Annalen der Chemie, 1977, p. 806 - 810
[3] Tetrahedron, 1998, vol. 54, # 35, p. 10265 - 10274
  • 8
  • [ 501-53-1 ]
  • [ 57224-63-2 ]
Reference: [1] Journal of the American Chemical Society, 1987, vol. 109, # 17, p. 5167 - 5175
[2] Tetrahedron, 1987, vol. 43, # 22, p. 5341 - 5349
  • 9
  • [ 74481-56-4 ]
  • [ 57224-63-2 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 4, p. 1037 - 1049
  • 10
  • [ 83824-81-1 ]
  • [ 57224-63-2 ]
Reference: [1] Journal of Organic Chemistry, 2000, vol. 65, # 4, p. 1037 - 1049
  • 11
  • [ 67-56-1 ]
  • [ 28130-04-3 ]
  • [ 57224-63-2 ]
Reference: [1] Synlett, 2010, # 14, p. 2141 - 2145
  • 12
  • [ 67-56-1 ]
  • [ 57224-63-2 ]
Reference: [1] Journal of Organic Chemistry, 1997, vol. 62, # 25, p. 8911 - 8913
  • 13
  • [ 186581-53-3 ]
  • [ 72-19-5 ]
  • [ 501-53-1 ]
  • [ 57224-63-2 ]
Reference: [1] Tetrahedron Letters, 1995, vol. 36, # 47, p. 8607 - 8610
  • 14
  • [ 57224-63-2 ]
  • [ 16966-09-9 ]
Reference: [1] Bulletin of the Chemical Society of Japan, 1982, vol. 55, # 9, p. 3049 - 3050
[2] Justus Liebigs Annalen der Chemie, 1963, vol. 670, p. 127 - 136
[3] Patent: CN106631900, 2017, A,
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