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[ CAS No. 42492-57-9 ] {[proInfo.proName]}

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Chemical Structure| 42492-57-9
Chemical Structure| 42492-57-9
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Product Details of [ 42492-57-9 ]

CAS No. :42492-57-9 MDL No. :MFCD04973115
Formula : C9H17NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :LTBDTYJYKRLTRN-UHFFFAOYSA-N
M.W : 203.24 Pubchem ID :14018930
Synonyms :

Calculated chemistry of [ 42492-57-9 ]

Physicochemical Properties

Num. heavy atoms : 14
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.78
Num. rotatable bonds : 6
Num. H-bond acceptors : 4.0
Num. H-bond donors : 0.0
Molar Refractivity : 51.27
TPSA : 55.84 Ų

Pharmacokinetics

GI absorption : High
BBB permeant : Yes
P-gp substrate : No
CYP1A2 inhibitor : No
CYP2C19 inhibitor : No
CYP2C9 inhibitor : No
CYP2D6 inhibitor : No
CYP3A4 inhibitor : No
Log Kp (skin permeation) : -6.81 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.63
Log Po/w (XLOGP3) : 1.03
Log Po/w (WLOGP) : 1.03
Log Po/w (MLOGP) : 0.83
Log Po/w (SILICOS-IT) : 0.11
Consensus Log Po/w : 1.13

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.35
Solubility : 9.02 mg/ml ; 0.0444 mol/l
Class : Very soluble
Log S (Ali) : -1.79
Solubility : 3.28 mg/ml ; 0.0161 mol/l
Class : Very soluble
Log S (SILICOS-IT) : -0.99
Solubility : 20.8 mg/ml ; 0.102 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 1.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.36

Safety of [ 42492-57-9 ]

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 [ 42492-57-9 ]

* 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 [ 42492-57-9 ]
  • Downstream synthetic route of [ 42492-57-9 ]

[ 42492-57-9 ] Synthesis Path-Upstream   1~15

  • 1
  • [ 42492-57-9 ]
  • [ 13734-36-6 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 3, p. 487 - 499
[2] Journal of Natural Products, 2003, vol. 66, # 2, p. 183 - 199
  • 2
  • [ 24424-99-5 ]
  • [ 13515-93-0 ]
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YieldReaction ConditionsOperation in experiment
90% With triethylamine In dichloromethane at 0 - 20℃; for 48 h; Inert atmosphere To a suspension of sarcosine (35.64 g, 0.40 mol) in 350 mL MeOH was added thionyl chloride (29.02 mL, 0.40 mol) dropwise at 0 °C. After complete addition the cooling bath was removed and the reaction mixture was stirred for 30 min at r.t. and refluxed for further 6 h. The resulting solution was concentrated in vacuum and the residue was dried in high vacuum over night at r.t. to afford sarcosine methyl ester.HCl as a white powder which was used in the next step without further purification; yield: 56.14 g (quant.); mp. 102 °C. 1H-NMR (300 MHz, CDCl3): δ = 9.76 (s, 2 H, NH2), 3.88 (t, J = 5.6 Hz, 2 H, H-2), 3.82 (s, 3 H, H-4)), 2.83 (t, J = 5.2 Hz, 3 H, H-3). 13C-NMR(75 MHz, CDCl3): δ = 166.7 (C-1), 53.3 (C-2), 48.9 (C-3), 33.4 (C-4).1 To a suspension of sarcosine methylester.HCl (59.80 g, 0.43 mol) and (Boc)2O (138.01 mL, 0.65 mol) in 1.0 L CH2Cl2 TEA (119.09 mL, 0.86 mol) was added dropwise at 0 °C. After complete addition the cooling bath was removed and the reaction mixture was stirred for two days at r.t. Aq. HCl (1 M) was added until the aqueous layer showed pH = 6. The resulting two layers were separated and the organic layer was washed with dist. H2O, dried (Na2SO4), concentrated in vacuum and volatile impurities were removed in high vacuum over night at r.t. to afford a clear oil; yield: 78.65 g (90 percent)
Reference: [1] Synthesis (Germany), 2017, vol. 49, # 4, p. 770 - 774
[2] Patent: EP1032561, 2004, B1, . Location in patent: Page 21
  • 3
  • [ 186581-53-3 ]
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YieldReaction ConditionsOperation in experiment
90% at 0℃; for 0.5 h; Boc-N-sarcosine methyl ester (18) was prepared by treating a solution of Boc-Sar- OH (1.0 g, 5.3 mmol) in 1 : 1 DCM/MeOH (25 mL) cooled to 0° C portionwise with diazomethane (2M solution, excess) until the reaction mixture turned slight yellow. The reaction was kept at 0° C for 30 min and then HOAc (2 drops) was added. The organic solvents were removed to afford 1.0 g (90percent) of 18.
Reference: [1] Patent: WO2008/145562, 2008, A1, . Location in patent: Page/Page column 40
  • 4
  • [ 13734-36-6 ]
  • [ 74-88-4 ]
  • [ 42492-57-9 ]
Reference: [1] Organic Letters, 2018, vol. 20, # 19, p. 6003 - 6006
[2] Tetrahedron, 2012, vol. 68, # 35, p. 7070 - 7076
  • 5
  • [ 24424-99-5 ]
  • [ 74-88-4 ]
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YieldReaction ConditionsOperation in experiment
27%
Stage #1: With sodium hydrogencarbonate In tetrahydrofuran; water for 18 h;
Stage #2: With sodium hydride In N,N-dimethyl-formamide at 0℃; for 0.5 h;
Stage #3: at 20℃; for 48 h;
Glycine methyl ester hydrochloride (50.0 g, 0.398 mol, 1 eq.) was added to a 1 L flask containing water (300 mL) and THF (200 mL). Sodium bicarbonate (37.8 g, 0.438 mol) was added portionwise, followed by di-tert-butyl dicarbonate (83.4 g, 0.382 mol). The reaction was stirred for 18 h, and then the separated organic phase was concentrated. The mixture was redissolved in EtOAC, washed with brine, dried over Na2SO4, and evaporated to give an oily product (72 g, 95percent). The oily product was dissolved in DMF (500 mL) and cooled to 0° C. To the mixture was added NaH (60percent, 18.3 g, 0.457 mol) portionwise. The mixture was then stirred for 30 min and MeI (81.1 g, 0.571 mol) was added at such a rate as to maintain a reaction temperature below 20° C. The mixture was stirred at RT for 48 h. The mixture was poured into ice water (1.5 L), extracted with MTBE (300 mL×2). The combined organics were washed with brine, dried over Na2SO4, and evaporated. Silica gel chromatography (PE:EtOAc 7:1) gave N-Boc-N-methyl glycine methyl ester (21 g, 27percent).
Reference: [1] Patent: US2015/72982, 2015, A1, . Location in patent: Paragraph 0195
  • 6
  • [ 31954-27-5 ]
  • [ 74-88-4 ]
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Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 3, p. 487 - 499
  • 7
  • [ 13734-36-6 ]
  • [ 6674-22-2 ]
  • [ 74-88-4 ]
  • [ 42492-57-9 ]
Reference: [1] Patent: US5494925, 1996, A,
[2] Patent: US5512576, 1996, A,
[3] Patent: US5541168, 1996, A,
[4] Patent: US5556909, 1996, A,
[5] Patent: US5602154, 1997, A,
  • 8
  • [ 4530-20-5 ]
  • [ 74-88-4 ]
  • [ 42492-57-9 ]
Reference: [1] Chemistry - A European Journal, 2010, vol. 16, # 39, p. 11954 - 11962
[2] Journal of Natural Products, 2003, vol. 66, # 2, p. 183 - 199
  • 9
  • [ 123-91-1 ]
  • [ 24424-99-5 ]
  • [ 5680-79-5 ]
  • [ 42492-57-9 ]
Reference: [1] Patent: US5747535, 1998, A,
  • 10
  • [ 123-91-1 ]
  • [ 24424-99-5 ]
  • [ 5680-79-5 ]
  • [ 42492-57-9 ]
Reference: [1] Patent: EP739886, 1996, A2,
  • 11
  • [ 614-45-9 ]
  • [ 31954-27-5 ]
  • [ 42492-57-9 ]
Reference: [1] Journal of the Chemical Society - Series Chemical Communications, 1991, # 20, p. 1475 - 1476
  • 12
  • [ 24424-99-5 ]
  • [ 42492-57-9 ]
Reference: [1] Journal of Organic Chemistry, 1988, vol. 53, # 3, p. 487 - 499
  • 13
  • [ 1070-19-5 ]
  • [ 13515-93-0 ]
  • [ 42492-57-9 ]
Reference: [1] Gazzetta Chimica Italiana, 1977, vol. 107, p. 381 - 385
  • 14
  • [ 42492-57-9 ]
  • [ 13515-93-0 ]
YieldReaction ConditionsOperation in experiment
100% With hydrogenchloride In 1,4-dioxane; dichloromethane at 0 - 20℃; for 1 h; General procedure: A solution of HCl (3.3 M) in dioxane (5 mL) was added to a stirred solution of Nα-Boc-protected peptide (1 mmol) in DCM (2 mL) at 0 °C. The temperature was risen to 20 °C and the solution maintained for 1 h. The solvents were removed under vacuum and the residue stirred in dry ether to produce a crystalline product. In case of the poorly crystallizing or highly hygroscopic compounds the residual material was dissolved in dry chloroform, the solution evaporated and the product dried in a vacuum desiccator over P4O10 or KOH. Some products were purified by chromatography using silica gel and eluent mixture B, or by gel filtration on biogel P2 or fractogel TCK HW 40 with subsequent lyophilization.
Reference: [1] Tetrahedron, 2012, vol. 68, # 35, p. 7070 - 7076
  • 15
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  • [ 123387-72-4 ]
Reference: [1] Journal of Natural Products, 2003, vol. 66, # 2, p. 183 - 199
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