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CAS No. : | 3401-36-3 | MDL No. : | MFCD00053548 |
Formula : | C15H16N2O6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OFIYNISEFIEQBC-JTQLQIEISA-N |
M.W : | 320.30 | Pubchem ID : | 837751 |
Synonyms : |
|
Chemical Name : | 2,5-Dioxopyrrolidin-1-yl ((benzyloxy)carbonyl)-L-alaninate |
Num. heavy atoms : | 23 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.33 |
Num. rotatable bonds : | 8 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 80.72 |
TPSA : | 102.01 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | Yes |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -7.64 cm/s |
Log Po/w (iLOGP) : | 1.83 |
Log Po/w (XLOGP3) : | 0.87 |
Log Po/w (WLOGP) : | 0.38 |
Log Po/w (MLOGP) : | 0.89 |
Log Po/w (SILICOS-IT) : | 0.69 |
Consensus Log Po/w : | 0.93 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.04 |
Solubility : | 2.93 mg/ml ; 0.00914 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.6 |
Solubility : | 0.812 mg/ml ; 0.00253 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -2.87 |
Solubility : | 0.432 mg/ml ; 0.00135 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.53 |
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 |
---|---|---|
General procedure: The N-Cbz-L-amino acid (1 mmol) and N-hydroxysuccinimide(1 mmol) were dissolved in dry THF at 0 C. Once a clear solutionhad been obtained, DCC (1 mmol) in anhydrous THF was added inseveral aliquots and the resulting solution was stirred at 0e5 C for3 h. The dicyclohexylurea formed was filtered off and the filtratewas concentrated to dryness. The crude product was recrystallizedfrom 2-propanol to furnish the pure product | ||
With bis(trichloromethyl) carbonate; triethylamine; In dichloromethane; at 0℃; for 0.5h; | General procedure: To a stirred solution of the carboxylic acid (2.0 mmol, 1.0 eq) in CH2Cl2 (10.0 ml) at 0C were added triphosgene (296.8 mg, 1.0 mmol, 1.5 eq), triethylamine (1.40 ml, 10.0 mmol,5.0 eq) and N-hydroxysuccinimide (230.2 mg, 2.0 mmol, 1.0 eq). After 30 min, amine(2.0 mmol, 1.0 eq) was added at 0C to the reaction mixture. The reaction mixture was stirred for 1 h at room temperature. The progress of the reaction was monitored by TLC. Removal of the solvent by rotary evaporation followed by short path silica gel column chromatography purification using 50% ethyl acetate in hexane as themobile phase afforded the pure product in high yields. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Part C: [(N-Benzyloxycarbonyl)Alaninyl]Aspartic Acid, [beta]-tert-Butyl Ester (0159) To a suspension of aspartic acid b-tert-butyl ester (3.784 g, 20 mmol) in dimethylformamide (150 mL) at room temperature under nitrogen was added bis(trimethylsilyl)-trifluoroacetamide (10.6 mL, 40 mmol). After stirring at room temperature for 30 min, the resulting clear solution was treated with (N-benzyloxycarbonyl) alanine N-hydroxysuccinimide ester (6.406 g, 20 mmol). After stirring at room temperature for 18 hours, the mixture was treated with water (20 mL), stirred for 15 minutes and then partitioned between ethyl acetate & water. The organic phase was washed with water, 5% potassium bisulfate and saturated sodium chloride solutions, dried over anhydrous sodium sulfate, and evaporated to dryness. The residue was then taken up in ethyl ether and extracted with saturated sodium bicarbonate. The aqueous extract was acidified (pH 2.0) with concentrated HCl and extracted with ethyl acetate. The ethyl acetate extract was washed with saturated sodium chloride solution, dried over anhydrous sodium Part D: (3S,4RS)-3-[(N-Benzyloxycarbonyl)Alaninyl]Amino-5-Bromo-4-Oxopentanoic Acid tert-Butyl Ester | ||
To a suspension of aspartic acid b-tert-butyl ester (3.784 g, 20 mmol) in dimethylformamide (150 mL) at room temperture under nitrogen was added bis(trimethylsilyl)15 trifluoroacetamide (10.6 mL, 40 mmol). After stirring at room temperature for 30 mm, theresulting clear solution was treated with (N-benzyloxycarbonyl) alanine N-hydroxysuccinimide ester (6.406 g, 20 mmol). After stirring at room temperature for 18 hours, the mixture was treated with water (20 mL), stirred for 15 minutes and then partitioned between ethyl acetate & water. The organic phase was washed with water, 5% potassium bisulfate and saturated sodium chloridesolutions, dried over anhydrous sodium sulfate, and evaporated to dryness. The residue was then taken up in ethyl ether and extracted with saturated sodium bicarbonate. The aqueous extract was acidified (pH 2.0) with concentrated HC1 and extracted with ethyl acetate. The ethyl acetate extract was washed with saturated sodium chloride solution, dried over anhydrous sodium Part |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; at 20℃; | To a solution of 1-{(f?)-1-[9-((1 f?,2S,3R,4S)-4-amino-2,3-dihydroxy-cyclopentyl)-6- (2,2-diphenyl-ethylamino)-9/-/-purin-2-yl]-py?olidin-3-yl}-3-pyridin-3-yl-urea (17 mg, 26 mumol) in THF (1 mL) is added Z-L-alanine hydroxysuccinimidyl ester (9 mg, 29 mumol) and the reaction mixture is stirred at RT overnight. The solvent is removed in vacuo and the crude residue is dissolved in EtOH (1 mL) and purged with argon. Ralladium on carbon (approximately 5 mg) is added and the reaction mixture is placed under a constant pressure of hydrogen (0.35 bar) and stirred at room temperature overnight. The resulting mixture is filtered through celite and concentrated in vacuo. Purification of the crude residue by reverse phase column chromatography (Isolute C18, 0-100% acetonitrile in water- 0.1% HCI) affords the title compound. [MH+732.72]. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | In ylformamide; diethyl ether; water; | Part A [(N-Benzyloxycarbonyl)Alaninyl]Aspartic Acid, beta-tert-Butyl Ester To a suspension of aspartic acid,-tert-butyl ester (3.784 g, 20 mmol) in ylformamide (150 mL) at room temperture under nitrogen was added bis(trimethylsilyl)-trifluoroacetamide (10.6 mL, 40 mmol). After stirring at room temperature for 30 min, the resulting clear solution was treated with (N-benzyloxycarbonyl)alanine N-hydroxysuccinimide ester (6.406 g, 20 mmol). After stirring at ronum temperature for an additional 48 hrs, the mixture was treated with water (20 mL), stirred for 15 min and then partitioned betweeen EtOAc/water. The organic phase was washed with water, 5% KHSO4 and saturated NaCl solutions, dried over anhydrous Na2SO4 and evaporated to a dryness. The residue was dissolved in Et2O and extracted with saturated NaHCO3. The aqueous extract was acidified (pH 2.0) with concentrated HCl and extracted with EtOAc. The EtOAc extract was washed with saturated NaCl solution, dried over anhydrous Na2SO4 and evaporated to a give the title compound (6.463 g, 82%) as a white foam. TLC(EtOAc-hexane-AcOH; 70:30:2) Rf=0.50. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; palladium-carbon; ethanol; ethyl acetate; triethylamine; | b) 320 mg of the product of the previous step in 10 ml of EtOH are hydrogenated in the presence of 100 mg of 10% Pd/C, the catalyst is filtered off after 2 hours and the residue in 10 ml of THF is stirred with 224 mg of N-benzyloxycarbonyl-L-alanine N-hydroxysuccinimide ester in the presence of 100 mul of triethylamine. The reaction solution is diluted with ether, the organic phase is washed with 1M KHSO4 solution, dried and evaporated. Chromatography of the residue on silica gel with hexane/ethyl acetate (1:1) gives 260 mg of t-butyl (S)-cis-1-(2-benzyloxycarbonylamino-propionyl)-4-t-butoxycarbonylmethoxy-pyrrolidin-3-yloxyacetate. MS: 537 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.48 g (80%) | With triethylamine; In dichloromethane; | a) N-Benzyloxycarbonyl-L-alanyl-L-argininal dibutylacetal hydrochloride N-Benzyloxycarbonyl-L-alanine-N-hydroxysuccinimide ester (0.53 g, 1.65 mmol) was used instead of N-benzyloxycarbonyl-L-pyroglutamyl-L-proline-N-hydroxysuccinimide ester and, a suspension of L-argininal dibutylacetal hydrochloride (0.49 g, 1.50 mmol) in methylene chloride (15 ml) and triethylamine (0.21 ml, 1.50 mmol) were reacted therewith in a manner similar to Example 1 a) to give 0.48 g (80%) of N-benzyloxycarbonyl-L-alanyl-L-argininal dibutylacetal hydrochloride as oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; methanol; diethyl ether; water; isopropyl alcohol; | While stirring at room temperature, a solution of 6.4 g (20 mmol) of N-benzyloxycarbonyl-L-alanine-N-hydroxysuccinimide ester in 200 ml of tetrahydrofuran is added dropwise over a period of 45 minutes to a solution of 7.6 g (60 mmol) of 1,3-diamino-2-propanol hydrochloride (Eastman, pract.) in 200 ml of water and the whole is stirred for 17 hours at room temperature. The solution is then concentrated to 50 ml and filtered and the filtrate is evaporated to dryness at 30 under a high vacuum. The resulting residue is purified by column chromatography over 2000 g of silica gel (Type 60, Merck; 0.063-0.2 mm) in the system chloroform/methanol (7:3, 20 ml fractions). Fractions 76-314 are combined and concentrated by evaporation at 30 under a high vacuum. The residue (white foam) crystallises from isopropanol/diethyl ether (1:7). N-benzyloxycarbonyl-L-alanine-3-amino-2-hydroxypropylamide hydrochloride is obtained in the form of colourless crystals that sinter at 96 and melt at from 114-116; [alpha]D20 =-18.9+-1.0 (c= 0.975; water), Rf =0.3 (chloroform:methanol:water =70:30:5). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In tetrahydrofuran; water; | The starting material is obtained as follows: Stage 10.1: 8.00 g (25 mmol) of N-benzyloxycarbonyl-L-alanine-N-hydroxysuccinimide ester are dissolved in 40 ml of absolute tetrahydrofuran and, while stirring, 1.53 g (25 mmol) of 2-aminoethanol, dissolved in 10 ml of tetrahydrofuran, are added dropwise thereto. After stirring for 4 hours, the resulting white suspension is filtered, the precipitate is washed with diethyl ether and the filtrate is evaporated to dryness. The residue is partitioned several times between ethyl acetate diethyl ether/petroleum ether and water. The aqueous phase is extensively concentrated, taken up in 80 ml of water that has been distilled twice and lyophilised. N-benzyloxycarbonyl-L-alanine-ethanolamide is obtained in the form of a colourless powder; [alpha]D20 =-14+-1 (c=0.484; water), Rf =0.60 (chloroform:methanol:water=70:30:5), Rf =0.77 (ethyl acetate:n-butanol:pyridine:acetic acid:water=42:21:21:6:10). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(iii) 11.5 g (36 mmol) of N-benzyloxycarbonyl-L-alanine N-hydroxysuccinimide ester were condensed with 8 g (24.5 mmol) of (1R)-1-(L-nitroarginylamino)-ethylphosphonic acid in a manner analogous to that described in the first paragraph of this Example. Working-up as described in said paragraph gave 13.92 g of monobenzylamine salt of melting point 210-215 C. (decomposition). Recrystallisation of a sample from a mixture of water, ethanol and diethyl ether gave the monobenzylamine salt of (1R)-1-[(N-benzyloxycarbonyl-L-alanyl-L-nitroarginyl)amino]-ethylphosphonic acid of melting point 228-230 C. (decomposition); [alpha]D20 =-31.5 (c=0.5% in acetic acid); [alpha]36520 =-117 (c=0.5% in acetic acid). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With sodium hydrogencarbonate; In 1,2-dimethoxyethane; water; | (a) To a stirred solution of 214.2 mg. of beta-fluoro-D-alanine and 420 mg. of sodium bicarbonate in 5 ml. of water was added a solution of 800.8 mg. of carbobenzoxy-L-alanine N-hydroxysuccinimide ester in 5 ml. of 1,2-dimethoxyethane. After stirring overnight at ambient temperature, the solution was concentrated to a syrup under reduced pressure. The residue was dissolved in 10 ml. of water and acidified with 1 N-hydrochloric acid to precipitate 521 mg. of N-carbobenzoxy-L-alanyl-beta-fluoro-D-alanine, m.p. 156-7 C. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
(i) In a manner analogous to that described in Example 1(B)(i), from N-benzyloxycarbonyl-L-alanine N-hydroxysuccinimide ester and (1R)-1-(L-norvalylamino)-ethylphosphonic acid there was obtained the monobenzylamine salt of (1R)-1-[(N-benzyloxycarbonyl-L-alanyl-L-norvalyl)amino]-ethylphosphonic acid of melting point 240-243 C. (decomposition). A sample was recrystallized from hot water to give 0.11 g of product of melting point 234-237 C. (decomposition); [alpha]D20 =-39.1; [alpha]36520 =-137 (c=0.49% in acetic acid). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With triethylamine; In tetrahydrofuran; water; | 1. Preparation of Z-Ala-Gln-OH To a solution of 4.80 g of <strong>[3401-36-3]Z-Ala-OSu</strong> in 60 ml of tetrahydrofuran was added a solution of 2.19 g of H-Gln-OH in 40 ml of water and 2.10 ml of triethylamine and the mixture was stirred at a room temperature for 20 hours. Tetrahydrofuran and water were removed by distillation and the residue thus obtained was extracted with n-butanol. The n-butanol extract was washed with a 2%-acetic acid and butanol was removed by distillation. The precipitated substance thus obtained was collected by filtration and reprecipitated with methanol-ethyl acetate to obtain 3.87 g of Z-Ala-Gln-OH. |
[ 3496-11-5 ]
(S)-2,5-Dioxopyrrolidin-1-yl 2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate
Similarity: 0.98
[ 4467-55-4 ]
(R)-2,5-Dioxopyrrolidin-1-yl 2-(((benzyloxy)carbonyl)amino)-3-methylbutanoate
Similarity: 0.98
[ 65581-25-1 ]
(R)-2,5-Dioxopyrrolidin-1-yl 2-(((benzyloxy)carbonyl)amino)-4-methylpentanoate
Similarity: 0.96
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