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CAS No. : | 61348-28-5 | MDL No. : | MFCD00038158 |
Formula : | C10H18N2O5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | VVNYDCGZZSTUBC-ZCFIWIBFSA-N |
M.W : | 246.26 | Pubchem ID : | 2724760 |
Synonyms : |
|
Num. heavy atoms : | 17 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.7 |
Num. rotatable bonds : | 8 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 59.38 |
TPSA : | 118.72 Ų |
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) : | -7.97 cm/s |
Log Po/w (iLOGP) : | 1.35 |
Log Po/w (XLOGP3) : | -0.24 |
Log Po/w (WLOGP) : | 0.23 |
Log Po/w (MLOGP) : | -0.17 |
Log Po/w (SILICOS-IT) : | -0.51 |
Consensus Log Po/w : | 0.13 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -0.69 |
Solubility : | 50.6 mg/ml ; 0.205 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.8 |
Solubility : | 3.95 mg/ml ; 0.016 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -0.66 |
Solubility : | 54.0 mg/ml ; 0.219 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 2.86 |
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: |
* 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.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
68% | With pyridine; acetic anhydride; at 20℃; for 20h; | 5.0 g (20.3 mmol) (R)-N-alpha-(tert.-butoxycarbonyl)-D-glutamine are combined with 2.30 ml (24.3 mmol) acetic anhydride in 55 ml of pyridine with stirring at room temperature and stirred for 20 h. The reaction mixture is evaporated down i. vac., the residue is combined with ethyl acetate and washed 3 times with 5% citric acid and 3 times with sat. NaCl solution. The organic phase is dried on sodium sulphate and concentrated by evaporation i.vac. Then it is purified by chromatography on silica gel (eluant: dichloromethane/methanol 90:10).Yield: 3.16 g (68%)Rf value: 0.3 (silica gel; dichloromethane/methanol=9:1)C10H16N2O4 (228.25)Mass spectrum: (M-H)-=227 |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Compound 11 or 12 (0.2 mmol) was treated with HCl/EtOAc (4 mol/L, 2 mL) for 1 h then concentrated in vacuo. The residue was redissolved in EtOAc (10 mL) and concentrated in vacuo again. The resulting solid was dried under vacuum for 2 h and then dissolved in 8 mL of dry DCM-DMF (3:1). After being cooled with an ice-water bath for 10 min, Fmoc-N-Me-D-Gln-OH (0.2 mmol) or <strong>[61348-28-5]Boc-D-Gln-OH</strong> (0.2 mmol), EDC (0.24 mmol), HOAt (0.24 mmol) and NaHCO3 (0.3 mmol) were added consecutively. The mixture was stirred at this temperature for 2 h and then at rt for another 12 h. The mixture was diluted with 80 mL of EtOAc and washed with 10% citric acid, 5% NaHCO3, water and brine. The organic layer was dried over Na2SO4, then concentrated in vacuo. The residue was purified by flash column chromatography to give the desired compounds 13a-c. These three compounds were used directly without further structural characterizations. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Compound 11 or 12 (0.2 mmol) was treated with HCl/EtOAc (4 mol/L, 2 mL) for 1 h then concentrated in vacuo. The residue was redissolved in EtOAc (10 mL) and concentrated in vacuo again. The resulting solid was dried under vacuum for 2 h and then dissolved in 8 mL of dry DCM-DMF (3:1). After being cooled with an ice-water bath for 10 min, Fmoc-N-Me-D-Gln-OH (0.2 mmol) or <strong>[61348-28-5]Boc-D-Gln-OH</strong> (0.2 mmol), EDC (0.24 mmol), HOAt (0.24 mmol) and NaHCO3 (0.3 mmol) were added consecutively. The mixture was stirred at this temperature for 2 h and then at rt for another 12 h. The mixture was diluted with 80 mL of EtOAc and washed with 10% citric acid, 5% NaHCO3, water and brine. The organic layer was dried over Na2SO4, then concentrated in vacuo. The residue was purified by flash column chromatography to give the desired compounds 13a-c. These three compounds were used directly without further structural characterizations. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; In ethyl acetate; at -15℃; for 0.25h; | These compounds were prepared by solution-phase peptide syntheses using Nalpha-<strong>[61348-28-5]Boc-D-Gln-OH</strong> (0.759 g, 3.08 mmol) and Nalpha-Boc-L-Gln-OH (0.759 g, 3.08 mmol), as starting materials. The Nalpha-Boc protected Gln was dissolved in ethyl acetate (45 mL) and cooled to -15 C. N,N-Diisopropylethylamine (0.398 g, 3.38 mmol) and isobutyl chloroformate (0.463 g, 3.38 mmol) were added consecutively to the stirred solution and stirred at -15 C for 15 min. After that, isobutylamine (0.248 g, 3.38 mmol) was added at 0 C. It was allowed to warm up to room temperature within 30 min and stirred for additional 2 h. After evaporation of the solvent, the resulting residue was distributed between water and ethyl acetate. The combined organic layer was washed with 5% (m/v) KHSO4 (50 mL) and 5% (m/v) KHCO3 (50 mL). The solution was dried (sicc. Na2SO4) and after filtration, the solvent was evaporated. The crude product was recrystallized from diethyl ether. The N-Boc group in compounds 12-13 was deprotected with 100% TFA at room temperature for 30 min. The product was precipitated with ice cold diethyl ether, solubilized in acetonitrile-water (50:50, v/v%) mixture, and lyophilized. The lyophilized product was dissolved in acetonitrile (5 mL) and treated with acetic anhydride (excess) for 1.5 h. The reaction mixture was diluted with water and lyophilized. The crude peptides were analysed and purified by RP-HPLC giving a yield of 70-80%. For analytical data, see Table 1. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
57.8% | With dmap; benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; acetonitrile; at 20℃; for 18h; | [00596] l-Isobutyl-2,3,4,9-tetrahydro- lH-pyrido[3,4-]indole (228 mg, 1.00 mmol), l-ethyl-3- (3-dimethylaminopropyl)carbodiimide-HCl (EDC-HC1) (192 mg, 1.00 mmol), 4- dimethylaminopyridine (DMAP) (12 mg, 0.10 mmol), hydroxybenzotriazole (HOBT) (51 mg, 0.33 mmol), and <strong>[61348-28-5](R)-5-amino-2-(tert-butoxycarbonylamino)-5-oxopentanoic acid</strong> (246 mg, 1.00 mmol) were all dissolved in acetonitrile (1.25 mL), dimethylformamide (DMF) (5 mL), and diisopropylethylamine (DIEA) (200 mu, 1.20 mmol). The reaction was stirred for 18 hours at RT. The reaction mixture was diluted with EtOAc (100 mL), washed with sat. NaCl (2 x 50 mL), 1M citric acid (3 x 25 mL), sat. NaHC03 (3 x 25 mL), and sat. NaCl (50 mL). The organic layer was dried (anhyd. Na2S04), filtered, and evaporated under vacuum. This material was further purified by silica gel (25-30 g) chromatography using: 4 fractions (200 mL) consisting of CH2C12, 4%, 4.5%, and 5% MeOH in CH2C12. Fractions containing product were combined, and the solvent was evaporated under vacuum, yielding a solid (264 mg, 57.8% yield; TLC Rf = 0.05 (4% MeOH in CH2CI2); HPLC Rt = 4.149 min). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; triethylamine; In N,N-dimethyl-formamide; at 0 - 25℃; for 12.25h; | A mixture of <strong>[61348-28-5](2R)-5-amino-2-(tert-butoxycarbonylamino)-5-oxo-pentanoic acid</strong> (1 .06 g, 4.30 mmol, 1 .2 equiv.), methyl (2S)-2-aminopropanoate hydrochloride (500 mg, 3.58 mmol, 1 equiv.), HOBt (532 mg, 3.94 mmol, 1 .1 equiv.) and TEA (797 mg, 7.88 mmol, 1 .10 ml_, 2.2 equiv.) in DMF (5 ml_) was cooled to 0 C and EDCI (755 mg, 3.94 mmol, 1 .1 equiv.) was added to the mixture. The reaction mixture was stirred at 0 SC for 15 min and at 25 C for 12 hr. The reaction mixture was filtered and concentrated under reduced pressure to give a residue which was purified by prep-HPLC (column: Phenomenex luna C18 250*50mm*10 um ; mobile phase: [water(0.1 %TFA)-ACN];B%: 10%-40%,20min). Methyl (2S)-2-[[(2R)-5- amino-2-(tert-butoxycarbonylamino)-5-oxo-pentanoyl]amino] propanoate (660 mg, 56%) was obtained as a white solid. |
10%Spectr. | With benzotriazol-1-yloxyl-tris-(pyrrolidino)-phosphonium hexafluorophosphate; benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 0 - 25℃; | (0247) To an oven-dried round bottom flask equipped with a stir bar was added a Boc-protected amino acid or carboxylic acid (1.0 equiv), the HC1-salt of the methyl ester-protected amino acid (1.0 equiv) and dry DMF (0.1-0.3 M). The starting materials were dissolved at room temperature and HOBt (Sigma Aldrich, 1.2 equiv) and PyBOP (Chem-Impex International, Inc) were added. The flask was then cooled to 0 C. and DIPEA (2.1 equiv) was added dropwise. The reaction mixture was warmed to room temperature overnight. The reaction mixture was then diluted with 5 reaction volumes of EtOAc or DCM and quenched by the addition of 1 reaction volume of aqueous 1 M HCl. The aqueous and organic layers were separated and the aqueous layer was extracted 2 more times with the same solvent (EtOAc or DCM). The combined organic layers were washed with saturated aqueous NaHCO3 and brine. The organic layer was dried over Na2SO4, filtered, and then concentrated in vacuo. The crude product was either used directly in the subsequent step or was purified as described for the individual compounds listed below. |
[ 57521-85-4 ]
(R)-2-((tert-Butoxycarbonyl)amino)pentanoic acid
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