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[ CAS No. 137401-45-7 ] {[proInfo.proName]}

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Chemical Structure| 137401-45-7
Chemical Structure| 137401-45-7
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Product Details of [ 137401-45-7 ]

CAS No. :137401-45-7 MDL No. :MFCD09835539
Formula : C10H17NO6 Boiling Point : -
Linear Structure Formula :- InChI Key :JLNKUZUBBRTYOA-UHFFFAOYSA-N
M.W : 247.25 Pubchem ID :11011022
Synonyms :

Calculated chemistry of [ 137401-45-7 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 0
Fraction Csp3 : 0.7
Num. rotatable bonds : 8
Num. H-bond acceptors : 6.0
Num. H-bond donors : 2.0
Molar Refractivity : 57.75
TPSA : 101.93 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) : -7.09 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.21
Log Po/w (XLOGP3) : 1.01
Log Po/w (WLOGP) : 0.53
Log Po/w (MLOGP) : 0.23
Log Po/w (SILICOS-IT) : -0.12
Consensus Log Po/w : 0.77

Druglikeness

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

Water Solubility

Log S (ESOL) : -1.48
Solubility : 8.16 mg/ml ; 0.033 mol/l
Class : Very soluble
Log S (Ali) : -2.74
Solubility : 0.45 mg/ml ; 0.00182 mol/l
Class : Soluble
Log S (SILICOS-IT) : -0.74
Solubility : 44.9 mg/ml ; 0.182 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 2.0 alert
Leadlikeness : 2.0
Synthetic accessibility : 3.08

Safety of [ 137401-45-7 ]

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 [ 137401-45-7 ]

* 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.

  • Downstream synthetic route of [ 137401-45-7 ]

[ 137401-45-7 ] Synthesis Path-Downstream   1~1

  • 1
  • [ 102831-44-7 ]
  • [ 137686-07-8 ]
YieldReaction ConditionsOperation in experiment
98% With potassium hydroxide; In ethanol; at 20℃; To a solution of diester 6 (27.51 g, 100 mmol) in absolute EtOH (100 mL) in a round bottom flask, a solution of KOH(5.60 g, 100 mmol, 1 equiv) in EtOH (60 mL) was added dropwise while stirring at room temperature. The reactionmixture was kept stirring for overnight. After the reaction was completed, 90% of solvent was removed by evaporated invacuo. The residue was dissolved in solution of 1M NaHCO3 (100 mL) and extracted with EtOAc. The aqueous phase wasthen acidified by KHSO4 (powder) at 0 oC and extracted with EtOAc. The organic phase was dried over anhydrousMgSO4, filtered, and evaporated to obtain the pure product 5? without a need of purification via column chromatography.Yield 98% (24.11 g). 1H NMR (400 MHz, DMSO-d6): delta 13.31 (brs, 1H), 7.44 (d, J = 7.8 Hz, 1H), 4.72 (d, J = 7.8 Hz,1H), 4.15 (m, 2H), 1.39 (s, 9H), 1.20 (t, J = 7.0 Hz, 3H). 13C NMR (100 MHz, DMSO-d6): delta 168.20, 167.63, 155.52,79.37, 61.75, 58.01, 28.53, 14.43. HRMS (ESI, positive mode): m/z 270.0970 [M+Na]+, calcd for [C10H17NO6Na]+:270.0948
85% Step 2 To a solution of 1,3-diethyl 2-[(tert-butoxy)carbonyl]amino}propanedioate XCVI (2.22 g, 8 mmol) in a mixture of ethanol/water (45 mL/5 mL) was added KOH (0.45 g, 8 mmol) in water (3 mL) dropwise. The reaction mixture was stirred for 1.5 hours. The ethanol was evaporated and the residue was acidified to pH=2 by 2 M HCl and washed by DCM. The organic layer was washed with brine and dried over MgSO4. The solvent was evaporated to give 2-[(tert-butoxy)carbonyl]amino}-3-ethoxy-3-oxopropanoic acid XCVII as crystals (1.68 g, 6.8 mmol, 85% yield). 1H NMR (CDCl3) 1.31 (t, J=7 Hz, 3H), 1.41-1.45 (m, 9H), 4.23-4.31 9m, 2H), 4.76 (d, J=4 Hz, 1H), 7.77 (d, J=4 Hz, 1H), 10.84 (brs, 1H); ESIMS found for C10H17NO6 m/z 248 (M+H).
35% With potassium hydroxide; In ethanol; at 20℃; for 4h; b) 2-{ r(fer?-butoxy)carbonyllamino|-3-ethoxy-3-oxopropanoic acid (1-68) Potassium hydroxide 85% (1.19 g; 21 mmol; 1 eq) was added to a solution of 1,3- diethyl 2-{ [(iert-butoxy)carbonyl]amino}propanedioate (1-67) (4.97 g; 18 mmol; 1 eq) in ethanol (23 mL). The reaction mixture was stirred at room temperature for 4 hours. After concentration to dryness, the residue was taken up in ethyl acetate (150 mL) and water (50 mL). The basic aqueous layer was extracted with ethyl acetate (2 x 50 mL) and acidified at 0C with a solution of hydrochloric acid IN until pH 2. The resulting acidic aqueous layer was extracted with ethyl acetate (3 x 50 mL). The combined organic layers were dried over sodium sulfate, filtered and concentrated under reduced pressure. The title compound, 2-{ [(ieri-butoxy)carbonyl]amino}-3- ethoxy-3-oxopropanoic acid was obtained in 35% yield (1.57 g) as a colorless oil. 1H NMR (DMSO-d6): delta (ppm) 1.2 (t, 3H), 1.39 (s, 9H), 4.13 (q, 2H), 4.62 (m, 1H), 7.33 (s, 1H); MS (ESI+): m/z = 148.0 [(M+H)-Boc]+ .
With potassium hydroxide; In ethanol; water; at 20℃; for 12h; Intermediate: 2-((tert-butoxycarbonyl)amino)-3-ethoxy-3-oxopropanoic acid To a solution of diethyl 2-((tert-butoxycarbonyl)amino)malonate (30 g, 109 mmol) in EtOH/H2O (675 mL/75 mL), a solution of KOH (7 g, 120 mmol) in H2O (45 mL) was added dropwise while stirring at 20 C. The reaction mixture was stirred at 20 C. for 12 hours. The ethanol was removed in vacuo and the residue was acidified to pH=2 by 2N HCl (aq.) and washed with dichloromethane. The organic layer was washed with brine and dried over Na2SO4, filtered and concentrated to give 2-((tert-butoxycarbonyl)amino)-3-ethoxy-3-oxopropanoic acid.

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