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[ CAS No. 42918-86-5 ] {[proInfo.proName]}

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Chemical Structure| 42918-86-5
Chemical Structure| 42918-86-5
Structure of 42918-86-5 * Storage: {[proInfo.prStorage]}
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Product Details of [ 42918-86-5 ]

CAS No. :42918-86-5 MDL No. :MFCD00077006
Formula : C12H15NO4 Boiling Point : -
Linear Structure Formula :- InChI Key :SZQMTCSQWUYUML-JTQLQIEISA-N
M.W : 237.25 Pubchem ID :7349998
Synonyms :

Calculated chemistry of [ 42918-86-5 ]

Physicochemical Properties

Num. heavy atoms : 17
Num. arom. heavy atoms : 6
Fraction Csp3 : 0.33
Num. rotatable bonds : 7
Num. H-bond acceptors : 4.0
Num. H-bond donors : 2.0
Molar Refractivity : 61.69
TPSA : 75.63 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) : -6.36 cm/s

Lipophilicity

Log Po/w (iLOGP) : 2.1
Log Po/w (XLOGP3) : 1.96
Log Po/w (WLOGP) : 1.62
Log Po/w (MLOGP) : 1.43
Log Po/w (SILICOS-IT) : 1.17
Consensus Log Po/w : 1.66

Druglikeness

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

Water Solubility

Log S (ESOL) : -2.34
Solubility : 1.07 mg/ml ; 0.00452 mol/l
Class : Soluble
Log S (Ali) : -3.17
Solubility : 0.159 mg/ml ; 0.000671 mol/l
Class : Soluble
Log S (SILICOS-IT) : -2.76
Solubility : 0.409 mg/ml ; 0.00172 mol/l
Class : Soluble

Medicinal Chemistry

PAINS : 0.0 alert
Brenk : 0.0 alert
Leadlikeness : 1.0
Synthetic accessibility : 2.6

Safety of [ 42918-86-5 ]

Signal Word:Warning Class:N/A
Precautionary Statements:P261-P305+P351+P338 UN#:N/A
Hazard Statements:H315-H319-H335 Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 42918-86-5 ]

* 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 [ 42918-86-5 ]

[ 42918-86-5 ] Synthesis Path-Downstream   1~85

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  • [ 4089-07-0 ]
  • <i>N</i>-((<i>S</i>)-2-benzyloxycarbonylamino-butyryl)-L-tyrosine amide [ No CAS ]
  • 3
  • [ 42918-86-5 ]
  • [ 4089-07-0 ]
  • [ 132562-61-9 ]
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  • [ 92235-10-4 ]
  • 5
  • [ 5292-43-3 ]
  • [ 42918-86-5 ]
  • 2-Amino-l-butyryl-glykolsaeure [ No CAS ]
  • 8
  • [ 1492-24-6 ]
  • [ 501-53-1 ]
  • [ 42918-86-5 ]
YieldReaction ConditionsOperation in experiment
77% With sodium carbonate; In tetrahydrofuran; water; at 0 - 20℃; for 16h; To a solution of (S)-2-aminobutanoic acid (11.2 g, 109 mmol) in THF (200 mL) and a 2 M aqueous sodium carbonate solution (65.2 ml, 130 mmol) was added dropwise at 0° C. benzyl carbonochloridate (17.06 mL, 119 mmol). After stirring at room temperature for 16 hours, the reaction mixture was extracted with H2O/TBME, the aqueous layer was acidified with HCl (2M in H2O) until pH=2 and extracted with EtOAc. The organic layer was dried over Na2SO4, filtered and the filtrate was concentrated to give the title compound (22.8 g, 77percent) as a colorless oil. The product was used in the next step without further purification. LC-MS: [M-H] 236.2; Rt 0.76 min; (LCMS method 1).
In potassium hydroxide; a) Preparation of N-benzyloxycarbonyl-2(S)-aminobutyric acid 10 g of 2(S)-aminobutyric acid (97 mmol) are dissolved in aqueous 4M KOH solution (100 ml) and the mixture is cooled to 0° C. 24.7 g of benzyl chloroformate (145 mmol) are added and the mixture is stirred while allowing its temperature to rise to room temperature over 2 hours 30 minutes. The mixture is then diluted with water (100 ml) and extracted with ether (2*200 ml). The aqueous phase is acidified to a pH<1 with concentrated HCl and is extracted with ethyl acetate (3*200 ml). The ethyl acetate fractions are combined and dried (Na2SO4) and the solvent is removed. A white solid is obtained. 1H-NMR (ppm): 7.32 (5H, s, ArCH); 5.22-5.28 (1H, d, NH); 5.10 (2H, s, Ph-CH2); 4.02-4.44 (1H, m, alpha-CH); 1.58-2.02 (2H, m, CH2); 0.9-1.2 (3H, t, CH3).
With hydrogenchloride; sodium hydroxide; sodium hydrogencarbonate; In diethyl ether; water; Reference Example 2 (2S)-2-[(Phenylmethoxy)carbonyl]aminobutyric Acid (Reference compound No. 2-1) Sodium hydrogencarbonate (1.34 g) is dissolved in water (10 ml), (2S)-2-aminobutyric acid (0.50 g) is added to the solution, and the mixture is stirred for five minutes. Then, a solution of benzyl chloroformate (1.4 ml) in diethyl ether (4.0 ml) is added dropwise to the mixture, and the whole is stirred at room temperature for five hours. A 0.1 N aqueous sodium hydroxide solution is added to the reaction mixture to basify it, and the whole is washed with diethyl ether. Then, 2 N hydrochloric acid is added to the mixture to acidify it, and the whole is extracted with ethyl acetate. The extract is washed with water and saturated brine successively and dried over anhydrous magnesium sulfate. The extract is concentrated under reduced pressure to give the titled compound. [alpha] D20 -15.3° (c=0.98, methanol); IR(Film,cm-1): 3325,2972,1713,1531.
  • 9
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  • [ 4124-76-9 ]
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  • 16
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  • 17
  • [ 67-56-1 ]
  • [ 42918-86-5 ]
  • (S)-2-<(benzyloxycarbonyl)amino>butanoic acid methyl ester [ No CAS ]
  • 18
  • [ 6066-82-6 ]
  • [ 42918-86-5 ]
  • [ 71447-81-9 ]
  • 19
  • 2-Benzyloxycarbonylamino-butyric acid 2-chloro-ethyl ester [ No CAS ]
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  • 20
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  • [ 7352-64-9 ]
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  • [ 50917-72-1 ]
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  • [ 16640-68-9 ]
  • [ 188054-58-2 ]
  • 23
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  • [ 190142-08-6 ]
  • 2-(N-benzyloxycarbonyl-(S)-2-aminobutyroyl)-2'-(N-benzyloxycarbonyl-L-leucinyl)carbohydrazide [ No CAS ]
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  • 30
  • [ 853208-69-2 ]
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  • {(S)-1-[(S)-1-((S)-2-Methoxy-tetrahydro-furan-3-ylcarbamoyl)-3-methyl-butylcarbamoyl]-propyl}-carbamic acid benzyl ester [ No CAS ]
  • 31
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  • [ 50-00-0 ]
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  • 36
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  • [ 922705-31-5 ]
  • 37
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  • 3-(benzyloxycarbonyl-methyl-amino)-pentanoic acid; compound with <i>tert</i>-butylamine [ No CAS ]
  • 38
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  • [ 271600-24-9 ]
  • 39
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  • [ 869307-76-6 ]
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  • [ 869307-74-4 ]
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  • [ 869307-77-7 ]
  • 42
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  • 3-((S)-2-Benzyloxycarbonylamino-butyrylamino)-5-fluoro-4-oxo-pentanoic acid [ No CAS ]
  • 43
  • [ 42918-86-5 ]
  • 3-(2-benzyloxycarbonylamino-butyrylamino)-5-fluoro-4-oxo-pentanoic acid <i>tert</i>-butyl ester [ No CAS ]
  • 44
  • [ 42918-86-5 ]
  • [(S)-1-((S)-1-{(1S,2R,3R,4S)-1-Benzyl-4-[(S)-2-(2-benzyloxycarbonylamino-butyrylamino)-3-methyl-butyrylamino]-2,3-dihydroxy-5-phenyl-pentylcarbamoyl}-2-methyl-propylcarbamoyl)-propyl]-carbamic acid benzyl ester [ No CAS ]
  • 46
  • [ 42918-86-5 ]
  • (S)-(+)-1-carbobenzoxy-5-ethyl-2-iminohydantoin [ No CAS ]
  • 47
  • [ 42918-86-5 ]
  • C13H15N3O3 [ No CAS ]
  • 49
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  • [ 143914-90-3 ]
  • 50
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  • [ 143915-05-3 ]
  • 51
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  • [ 143915-04-2 ]
  • 52
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  • (S)-N-methyl-1-(pyrrolidin-1-yl)butan-2-amine [ No CAS ]
  • 53
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  • [ 136328-83-1 ]
  • 54
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  • [ 17327-61-6 ]
  • 55
  • [ 185212-12-8 ]
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  • [ 68641-49-6 ]
  • [ 185212-13-9 ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In tetrahydrofuran; ethyl acetate; Preparation of 1-(N-benzyloxycarbonyl-2(S)-aminobutyryl)-3,3-dimethylindoline-2(R/S)-carboxylic Acid Butylamide 3,3-Dimethylindoline-2(R/S)-carboxylic acid butylamide (1.000 g, 4.08 mmol) and N-benzyloxycarbonyl-2(S)-aminobutyric acid (1.451 g, 6.12 mmol) were dissolved in dry tetrahydrofuran (25 ml). The solution was cooled to 0° C. and triethylamine (2.44 ml, 13.78 mmol) and bis(2-oxo-3-oxazolidinyl)phosphinyl chloride (2.338 g, 9.183 mmol) were added. The mixture was stirred at room temperature for 22 hours and ethyl acetate (40 ml) was then added, and the mixture was washed with 3N hydrochloric acid (3*50 ml), 5percent sodium bicarbonate (3*50 ml) and water (50 ml) and dried over sodium sulphate. After removing the solvent, several successive purifications by chromatography on a column of silica gel gave the product in the form of an off-white solid. 1H-NMR (CDCl3), delta (ppm) 8.08-8.2 (1H, m, CONH), 7.02-7.5 (9H, m, ArH), 4.04-5.82 (5H, m, CH2 of the benzyl, CH, NH of the Abu, COCHN of the indoline), 3.00-3.30 (2H, m, CONCH2), 0.70-1.98 (18H, m, CH2CH3 of the Abu, 2*CH3 of the indoline, CH2CH2CH3 of the butyl).
  • 56
  • [ 6066-82-6 ]
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  • [ 219812-79-0 ]
  • (S)-3-[(2S,3R,4R,5S)-5-((S)-2-aminobutyryl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionic acid hydrochloride [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine;palladium on activated carbon; In N-methyl-acetamide; hydrogenchloride; methanol; acetonitrile; EXAMPLE 33 (S)-3-[(2S,3R,4R,5S)-5-((S)-2-aminobutyryl)amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionic acid hydrochloride To a solution of (S)-2-(benzyloxycarbonylamino)butyric acid (500 mg) in acetonitrile (10 ml) were added N-hydroxysuccinimide (291 mg) and N,N'-dicyclohexylcarbodimide (561 mg) at room temperature and the mixture was stirred at room temperature for 3 hours. The formed insoluble solid was filtrated off and the filtrate was added to a solution of (S)-3-[(2S,3R,4R,5S)-5-amino-2,3,4,6-tetrahydroxyhexanoyl]amino-3-phenylpropionic acid (compound 5) (722 mg) and triethylamine (0.558 ml) in dimethylformamide (50 ml). The mixtute was stirred at room temperature for 18 hours and concentrated under reduced pressure. To the residue was added 1N hydrochloric acid (50 ml) and the whole was extracted with ethyl acetate-tetrahydrofuran (1:1, 50 ml*3). The organic layer was washed with saturated brine and dried over anhydrous sodium sulfate. Removal of the organic solvent gave a residue, which was dissolved in methanol (50 ml) and stirred at room temperature with 10percent palladium on activated carbon (200 mg) under hydrogen atmosphere for 1 hour. After filtration, the filtrate was concentrated under reduced pressure to give a residue, which was dissolved in 0.1N hydrochloric acid (0.1 ml) and passed through a column of DIAION HP-20SS (Mitsubishi kasei corporation), followed by elution with water-acetonitrile. The effective fractions were combined and concentrated under reduced pressure. The residue was recrystallized from methanol-ethyl acetate to afford the title compound (200 mg). 1H-NMR(CD3OD) delta: 1.05(3H,t,J=7.6 Hz), 1.85-1.96(2H,m), 2.74(2H,d,J=6.4 Hz), 3.68-3.91(5H,m), 4.30-4.33(2H,m), 5.32(1H,t,J=6.4 Hz), 7.24-7.42(5H,m).
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  • [ 185213-14-3 ]
YieldReaction ConditionsOperation in experiment
c) Preparation of 1-(N-benzyloxycarbonyl-2(S)-aminobutyryl)-2(S)-indolinecarboxylic acid ethylamide The process is performed as in Example 16 d), using N-benzyloxycarbonyl-2(S)-aminobutyric acid prepared in Example 3 a) and the compound from step b). The pure amide is obtained in the form of a white solid. m.p.=184.5-185° C. 1H-NMR (400 MHz, CDCl3, ppm): 8.15 (1H, d, H aromatic J=7.9 Hz); 7.44-7.08 (8H, m, ArH); 7.04 (broad s, NH amide); 5.37 (1H, d, NH amide); 5.0-5.2 (2H, m, PhCH2); 4.84 (1H, m, alphaH); 4.18 (1H, m, alphaH); 3.62-3.48 (2H, m, CH2 indoline); 3.34-3.14 (2H, m, CH2 ethylamide); 2.10-1.60 (2H, m, CH2 aminobutyryl); 1.20-0.98 (3H, m, CH3).
  • 58
  • [ 42918-86-5 ]
  • [ 543-27-1 ]
  • [ 185213-06-3 ]
YieldReaction ConditionsOperation in experiment
With N-ethylmorpholine;; In (2S)-indolinecarboxylic acid propylamide; tetrahydrofuran; c) Preparation of 1-(N-benzyloxycarbonyl-2(S)-aminobutyryl)-2(S)-indolinecarboxylic acid n-propylamide 0.439 g (1.85 mmol) of N-benzyloxycarbonyl-2(S)-aminobutyric acid prepared as in Example 3 a) is dissolved, under nitrogen, in tetrahydrofuran (50 ml) and the solution is cooled in an ice/water bath. 0.213 g (1.85 mmol) of N-ethylmorpholine is added, followed by 0.253 g (1.85 mmol) of isobutyl chloroformate. After 45 minutes, 0.378 g (1.85 mmol) of the compound obtained in step b) is added and stirring is continued for 12 hours. The suspension is poured into CH2Cl2 (100 ml) and the mixture is washed with 10percent citric acid (3*100 ml) and then with 5percent NaHCO3 (3*100 ml). After drying and evaporation, a white solid is obtained which crystallizes from CCl4. m.p.=176-177° C. 1H-NMR (CDCl3, ppm: 7.0-7.25 (9H, m, H-Ar); 5.0 (2H, s, CH2 benzyloxycarbonyl); 4.8 (1H, m, aH); 4.1 (1H, alphaH); 3.3 (2H, m, CH2 ring); 3.0 (2H, m, CH2N); 1.0-2.0 (4H, m, CH3CH2CH2N CH2 aminobutyryl); 0.70-1.00 (CH3 aminobutyryl CH3 propyl).
  • 59
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  • [ 501-53-1 ]
  • [ 42918-86-5 ]
YieldReaction ConditionsOperation in experiment
With potassium carbonate; In water; Referential Example 1 Synthesis of 3(S)-[(t-butoxycarbonyl)amino]-gamma-butyrolactone Into 800 ml of water were dissolved 66.6 g of L-aspartic acid and 90.9 g of potassium carbonate, and 46.4 ml of carbobenzoxy chloride were added dropwise. After stirring the mixture for 2 hours at room temperature, 40.0 g of potassium carbonate were added and 46.4 ml of carbobenzoxy chloride were added dropwise, which was further stirred for 4 hours at room temperature. After washing the reaction liquor with ether, the pH was brought to 2 with concentrated hydrochloric acid, which was extracted with ethyl acetate. The ethyl acetate layer was separated, dried over anhydrous Glauber's salt, and then concentrated. The residue was crystallized with ether-n-hexane and the crystals deposited were collected by filtration, and then washed with n-hexane to obtain 108.6 g of 2(S)-[(benzyloxycarbonyl)amino]butanoic diacid.
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  • [ 305859-68-1 ]
YieldReaction ConditionsOperation in experiment
With hydrogenchloride; sodium borohydrid; acetic anhydride; toluene-4-sulfonic acid; In tetrahydrofuran; water; benzene; To 100 ml of acetic anhydride were added 106.9 g of 2(S)-[(benzyloxycarbonyl)amino]butanoic diacid, and the mixture was stirred for 2 hours at room temperature. The reaction liquor was concentrated below 40°C and the residue was washed with ether-n-hexane (5:1). 600 ml of anhydrous tetrahydrofuran (THF) dissolved these crystals and the solution was added dropwise to a solution of 500 ml of anhydrous tetrahydrofuran containing 14.4 g of dissolved sodium borohydride at 0°C, which was then stirred for 1 hr at room temperature. To the reaction liquor was added 6N hydrochloric acid to bring the pH to 2, and the solution was concentrated to about 1/4 by volume and extracted with ether after added water. The ether layer was separated, washed with water and then washed with saturated saline solution, and then concentrated. To the residue were added 200 ml of benzene and 0.4 g of p-toluenesulfonic acid, and the mixture was refluxed for 4 hours under heat. The reaction liquor was concentrated and the residue was crystallized with n-hexane-ether to obtain 82.5 g of 3(S)-[(benzyloxycarbonyl)amino]-gamma-butyrolactone as colorless prismatic crystals.
  • 61
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  • [ 530-62-1 ]
  • [ 1114547-07-7 ]
YieldReaction ConditionsOperation in experiment
Then, a solution of benzyl[(1S)-1-(1H-imidazol-1-ylcarbonyl)propyl]carbamate prepared from <strong>[42918-86-5](2S)-2-[(benzyloxy)carbonyl]amino}butanoic acid</strong> (50 g) and N,N'-carbonyldiimidazole (39.5 g) in tetrahydrofuran (300 mL) was added dropwise at -78° C. After stirring at -78° C. for 1 hr, acetic acid was added to the reaction mixture.
  • 62
  • [ 42918-86-5 ]
  • (1R)-3-methyl-1-[(1S,2S,6R,8S)-2,9,9-trimethyl-3,5-dioxa-4-boratricyclo[6.1.1.02,6]decan-4-yl]butan-1-amine [ No CAS ]
  • C27H41BN2O5 [ No CAS ]
  • 63
  • [ 110-91-8 ]
  • [ 42918-86-5 ]
  • [ 1355039-65-4 ]
YieldReaction ConditionsOperation in experiment
Preparation of Compound 12Step 1:(S)-2-amino-l-morpholinobutan-l-one hydrochloride. ("S)-2-(((benzyloxy)carbonyl)amino)butanoic acid (250 mg, 1.05 mmol) was mixed with HBTU ( 0.5M in DMF, 2.13 mL, 1.16 mmol), and DIEA (550 uL, 3.16 mmol), and morpholine (1 15 uL, 1.32 mmol), and stirred at RT for two hours, after which HPLC shows the reaction complete. Added brine (10 mL), and extract with EtOAc (2x10 mL). Pass organic extract through a plug of silica gel (2g, bond-elute), and wash with excess EtOAc until no additional product elutes. Combined homogeneous fractions, and removed EtOAc under vacuum. Dissolved in MeOH (3 mL) and stirred under 1 atmosphere of hydrogen using a balloon in the presence of 10percent Pd/C for a period of 16 hours. Filtered the reaction through a pad of celite, and wash with additional MeOH (3x5 mL). Starting material was consumed by tic and a more polar spot that stained with ninhydrin confirmed product formation. Used as is without further purification or charactarization in the next step.
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  • [ 104871-99-0 ]
  • [ 1398817-33-8 ]
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  • [ 578-66-5 ]
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  • [ 1449300-02-0 ]
  • 67
  • trimethylsilyl diazomethane [ No CAS ]
  • [ 42918-86-5 ]
  • (S)-2-<(benzyloxycarbonyl)amino>butanoic acid methyl ester [ No CAS ]
YieldReaction ConditionsOperation in experiment
48% In methanol; toluene; at 20℃; for 1h;Inert atmosphere; To a solution of <strong>[42918-86-5](S)-2-(((benzyloxy)carbonyl)amino)butanoic acid</strong> (10.0 g, 42.1 mmol) in methanol (100 mL) and toluene (300 mL) was added dropwise at room temperature under argon trimethylsilyldiazomethane (23.2 mL, 46.4 mmol). After stirring at room temperature for 1 hour, the reaction mixture was concentrated and the residue was extracted with a solution of EtOAc and brine. The combined organic layers were dried over Na2SO4, filtered and the filtrate was concentrated. The residue was purified by column chromatography (120 g SiO2) using EtOAc in hexane from 0percent to 30percent in order to give the title compound (5.2 g, 48percent) as a colorless oil. LC-MS: [M+H] 252.1; Rt 0.93 min; (LCMS method 1).
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  • [ 1609551-07-6 ]
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  • [ 75-64-9 ]
  • [ 1619922-67-6 ]
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  • [ 42918-86-5 ]
  • methyl 2-[(1S)-1-[(benzyloxy)carbonyl]amino}propyl]-1-methyl-1H-1,3-benzodiazole-6-carboxylate [ No CAS ]
  • 71
  • [ 42918-86-5 ]
  • methyl 1-methyl-2-[(1S)-1-{2-[(4-phenoxyphenyl)amino]acetamido}propyl]-1H-1,3-benzodiazole-6-carboxylate [ No CAS ]
  • 72
  • [ 42918-86-5 ]
  • methyl 2-[(1S)-1-[2,5-dioxo-3-(4-phenoxyphenyl)imidazolidin-1-yl]propyl]-1-methyl-1H-1,3-benzodiazole-6-carboxylate [ No CAS ]
  • 73
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  • 2-[(1S)-1-[2,5-dioxo-3-(4-phenoxyphenyl)imidazolidin-1-yl]propyl]-1-methyl-1H-1,3-benzodiazole-6-carboxylic acid [ No CAS ]
  • 74
  • [ 616224-38-5 ]
  • [ 42918-86-5 ]
  • methyl 4-[(2S)-2-[(benzyloxy)carbonyl]amino}butanamido]-3-(methylamino)benzoate [ No CAS ]
YieldReaction ConditionsOperation in experiment
45% With 1-hydroxy-7-aza-benzotriazole; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; trimethylamine; In N,N-dimethyl-formamide; at -20 - 0℃; for 15h; General procedure: To a solution of Z-Leu-OH (350 mg, 1.32 mmol) in DMF (3 ml), methyl 4-amino-3-(methylamino)benzoatee [3] (334 mg, 1.32 mmol) in DMF (2 ml) and trimethylamine (462 mul, 3.30 mmol) were added at 0 . Subsequently, HOAt (269 mg, 1.98 mmol) and WSCI.HCl (380 mg, 1.98 mmol) were added to the former solution at -20 °C and stirred for 15 h at ambient temperature. The reaction mixture was quenched with sat.NH4Cl and extracted with EtOAc. The combined extracts were washed with water and brine, dried over MgSO4 and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to give 278 mg of 1a
  • 75
  • [ 42918-86-5 ]
  • [ 1114547-11-3 ]
  • 76
  • [ 42918-86-5 ]
  • [ 1114547-13-5 ]
  • 77
  • [ 42918-86-5 ]
  • [ 141-78-6 ]
  • [ 1114547-09-9 ]
YieldReaction ConditionsOperation in experiment
62% To a solution of diisopropylamine (44.3 mL, 311 mmol) in THF(100 mL), 1.6 M n-butyl lithium solution in hexane (198 mL,317 mmol) was added dropwise at 78 C. After stirring at78C for 1 h, EtOAc (30.9 mL, 316 mmol) was added dropwiseat 78 C. The mixture was stirred at 78 C for 1 h, and then asolution of the compound, which was prepared from <strong>[42918-86-5](2S)-2-[(benzyloxy)carbonyl]amino}butanoic acid</strong> (8, 25.0 g, 105 mmol) andcarbonyldiimidazole (20.5 g, 126 mmol)] in THF (100 mL), wasadded dropwise to the mixture at 78 C. After stirring at 78 Cfor 1 h, acetic acid (25 mL) was added to quench the reaction andwarmed up to room temperature. The mixture was poured intowater and extracted with EtOAc. The organic layer was washedwith brine, dried over MgSO4 and concentrated in vacuo. The residuewas purified using silica gel column chromatography (n-hexaneto n-hexane:EtOAc = 2:1) to give 9 (20.0 g, 65.1 mmol, 62percent)as a colorless oil. 1H NMR (300 MHz, CDCl3) d 0.92 (3H, t,J = 7.5 Hz), 1.27 (3H, t, J = 7.2 Hz), 1.60?1.72 (1H, m), 1.91?2.09(1H, m), 3.47?3.61 (2H, m), 4.11?4.25 (2H, m), 4.40?4.51 (1H,m), 5.11 (2H, s), 5.41 (1H, d, J = 7.0 Hz), 7.31?7.39 (5H, m).
  • 78
  • [ 42918-86-5 ]
  • C14H16N2O3 [ No CAS ]
  • 79
  • [ 42918-86-5 ]
  • (S)-1-benzyloxycarbonyl-2-ethylpiperazin-3-one [ No CAS ]
  • 80
  • [ 42918-86-5 ]
  • (S)-1-benzyloxycarbonyl-4-(4-methoxyphenyl)-2-ethylpiperazin-3-one [ No CAS ]
  • 81
  • [ 42918-86-5 ]
  • [ 22483-09-6 ]
  • C16H24N2O5 [ No CAS ]
YieldReaction ConditionsOperation in experiment
98% With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 0.5h; (S) -2- (benzyloxycarbonylamino) butanoic acid (12-1) (2 g, 8.4 mmol),Dimethoxyethanamine (886 mg, 8.4 mmol)Was dissolved in dry DMF (45 mL)HBTU (3950 mg, 10.21 mmol)And DIEPA (3292 mg, 25.0 mmol),After the reaction mixture was magnetically stirred at room temperature for 30 minutes, water and ethyl acetate were added,The organic phase was separated and the aqueous phase was extracted with ethyl acetate. The combined extracts were washed with brine, dried over anhydrous sodium sulfate,After concentration under reduced pressure, 2.7 g of (12-2) (2.7 g) was isolated and purified by preparative thin-layer chromatography to give a 98percent yield of (S) -2-benzyloxycarbonylaminobutyric acid.
  • 82
  • [ 42918-86-5 ]
  • [ 6638-79-5 ]
  • (S)-benzyl (1-(methoxy(methyl)amino)-1-oxobutan-2-yl)carbamate [ No CAS ]
  • 83
  • [ 42918-86-5 ]
  • benzyl (1-(2-cyclopropylpyrimidin-5-yl)-1-oxobutan-2-yl)carbamate [ No CAS ]
  • 84
  • [ 42918-86-5 ]
  • benzyl 1-(2-cyclopropylpyrimidin-5-yl)-1-hydroxybutan-2-ylcarbamate [ No CAS ]
  • 85
  • [ 42918-86-5 ]
  • tert-butyl (2S,4S)-4-fluoro-2-((5-fluoro-2-(6-fluoro-3-(((S)-pyrrolidin-2-yl)methyl)-1H-indol-2-yl)-1H-benzo[d]imidazol-1-yl)methyl)pyrrolidine-1-carboxylate [ No CAS ]
  • tert-butyl (2S,4S)-2-((2-(3-(((S)-1-((S)-2-(((benzyloxy)carbonyl)amino)butanoyl)pyrrolidin-2-yl)methyl)-6-fluoro-1H-indol-2-yl)-5-fluoro-1H-benzo[d]imidazol-1-yl)methyl)-4-fluoropyrrolidine-1-carboxylate [ No CAS ]
YieldReaction ConditionsOperation in experiment
To a solution of N-Boc-L-n-butyric acid(122.13 mg, 514.8 mumol) in DMF (1 mL) wereadded HATU (195.74 mg, 514.8 mumol) and N-methylmorpholine (1.03 mmol, 113.20 muL), the mixture was stirred for 15 min at 10-20°C, and then added with a solution of tert-butyl (2S,4S)-4-fluoro-2-((5-fluoro-2-(6-fluoro-3-(((S)-pyrrolidin-2-yl)methyl)-1H-indol-2-yl)-1H-benzo[d]imidazol-1-yl)methyl)pyrrolidine-1-carboxylate (crude product, 190.00 mg, 343.20 mumol) in DMF (2 mL). After stirring for 16 h at 10-20°C, the mixture was added with water (30 mL) and extracted with EtOAc (50 mL). The organic phase was separated, washed with sat.aq. NaCl (50 mL), dried over anhydrous Na2SO4, filtered and the filtrate was concentrated in vacuo to give crude product, tert-butyl (2S,4S)-2-((2-(3-(((S)-1-((S)-2-(((benzyloxy)carbonyl)amino)butanoyl)pyrrolidin-2-yl )methyl)-6-fluoro-1H-indol-2-yl)-5-fluoro-1H-benzo[d]imidazol-1-yl)methyl)-4-fluor opyrrolidine-1-carboxylate (300.00 mg). MS (ESI) m/z: 773.2 [M+H+]
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