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[ CAS No. 191103-80-7 ]

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Chemical Structure| 191103-80-7
Chemical Structure| 191103-80-7
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Product Details of [ 191103-80-7 ]

CAS No. :191103-80-7 MDL No. :MFCD06203351
Formula : C23H18N2O2 Boiling Point : 546.287°C at 760 mmHg
Linear Structure Formula :- InChI Key :-
M.W :354.40 g/mol Pubchem ID :-
Synonyms :

Safety of [ 191103-80-7 ]

Signal Word:Warning Class:
Precautionary Statements:P261-P280-P301+P312-P302+P352-P305+P351+P338 UN#:
Hazard Statements:H302-H315-H319-H335 Packing Group:
GHS Pictogram:

Application In Synthesis of [ 191103-80-7 ]

  • Downstream synthetic route of [ 191103-80-7 ]

[ 191103-80-7 ] Synthesis Path-Downstream   1~9

  • 1
  • [ 76-83-5 ]
  • [ 1072-84-0 ]
  • [ 191103-80-7 ]
YieldReaction ConditionsOperation in experiment
99.7% With pyridine; In N,N-dimethyl-formamide; at 50℃; for 6h; 1H-<strong>[1072-84-0]imidazole-4-carboxylic acid</strong>(5.0 g, 44.6 mmol) and triphenylchloromethane (13.8 g, 49.1 mmol)It was added to a mixture of 50 ml of DMF and 2.5 ml of pyridine. After the addition, the temperature is raised to 50 ° C for 6 h.The reaction was detected by HPLC. Post-treatment: The system is cooled, and the reaction system is slowly added to 100 ml of water.The gray solid precipitated, and the suspension was stirred for 1 hour and then filtered.The filter cake was washed with a small amount of water, dried for 30 min, and dried under vacuum at 50 ° C to obtain 15.8 g of a gray solid.Yield: 99.7percent.
95% With pyridine; In N,N-dimethyl-formamide; at 20℃; 1-(Triphenylmethyl)-1H-<strong>[1072-84-0]imidazole-4-carboxylic acid</strong> was prepared as described in J. Med. Chem. 2001, 44, 1268. 1 H-lmidazole-4-carboxylic acid (0.50 g, 4.5 mmol) and trityl chloride (1.35 g, 4.9 mmol) were added to a solution of DMF (30 ml.) and pyridine (15 ml.) and stirred overnight. Water and EtOAc were added. The layers were separated and the aqueous layer extracted with EtOAc (2 x 50 ml_). The organic extracts were combined, washed with water and brine, dried over Na2SO4, filtered and evaporated. The oil was triturated with EtOAc to afford the title compound (1.5 g, 95percent) as a white solid. 1H NMR (400 MHz, DMSO-d6): delta ppm 12.40 (br. s., 1 H), 7.42 (t, 9 H), 7.17 - 7.35 (m, 2 H), 7.10 (d, 6 H). MS: m/z 1 11 (M-243).
79% With pyridine; In N,N-dimethyl-formamide; at 20℃; Example 6; To a RT solution of 1H-<strong>[1072-84-0]imidazole-4-carboxylic acid</strong> (1.12 g, 9.99 mmol) in pyridine (15 mL) and DMF (30 mL) was added triphenylmethyl chloride (3.06 g, 11.0 mmol). The reaction mixture was stirred at RT overnight, then was partitioned between EtOAc (500 mL) and H2O (50 mL). The organic phase was washed with H2O (20 mL), 10percent citric acid (20 mL) and brine (5 mL), dried (MgSO4) and concentrated in vacuo. The residue was triturated with EtOAc to afford 1-trityl-1H-<strong>[1072-84-0]imidazole-4-carboxylic acid</strong> (2.78 g, 79percent yield) as a white solid. LCMS Method A (ESI, positive ion spectrum): (M+H)/z=not observed, tR=3.27 min.
  • 2
  • [ 191103-80-7 ]
  • [ 123066-64-8 ]
  • 4'-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]-1H-imidazole-4-carboxanilide [ No CAS ]
YieldReaction ConditionsOperation in experiment
A mixture of 1-trityl-1H-imidazole-4-carboxylic acid (300 mg), <strong>[123066-64-8]4-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]aniline</strong> (200 mg), WSCD hydrochloride (162 mg), DMF (0.5 ml) and THF (4 ml) was stirred overnight at room temperature. Water (10 ml) was added to the reaction solution, the thus formed product was extracted with ethyl acetate and then the extract was washed with saturated brine. The organic layer was dried over anhydrous magnesium sulfate and then concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=3:1). Then, concentrated hydrochloric acid (0.1 ml) and acetone (3 ml) were added, followed by stirring overnignt at room temperature. The reaction solution was concentrated under a reduced pressure, diethyl ether was added to the thus obtained residue, and when the mixture was concentrated under a reduced pressure. A mixed solvent of ethanol and diethyl ether was added to the thus obtained residue, time insoluble matter was removed by filtration and then the filtrate was concentrated under a reduced pressure. The resulting residue was purified by silica gel column chromatography (eluent; n-hexane:ethyl acetate=1:1-2:3) and then recrystallized from a mixed solvent of ethyl acetate and n-hexane, thereby obtaining [4'-[3,5-bis(trifluoromethyl)-1H-pyrazol-1-yl]-1H-imidazole]-4-carboxyanilide (35 mg) as colorless powder crystals.
  • 3
  • [ 76074-88-9 ]
  • [ 191103-80-7 ]
YieldReaction ConditionsOperation in experiment
95.1% With aqueous hydrochloric acid; aqueous sodium hydroxide In methanol 67.2 Step 2 Step 2 Preparation of 1-trityl-1H-imidazole-4-carboxylic acid A solution of 1-trityl-1H-imidazole-4-carboxylic acid methyl ester (1.75 g, 4.60 mmol) in methanol (50 mL) at 25° C. was treated with a 1N aqueous sodium hydroxide solution (13.8 mL, 13.8 mmol). The reaction was stirred at 25° C. for 18 h and then heated to 50° C. for 1.5 h. At this time, the reaction was cooled to 25° C. and diluted with water (150 mL). The aqueous layer was brought to pH=1 by treatment with a 1N aqueous hydrochloric acid solution and then diluted with ethyl acetate (250 mL). The resulting precipitated product was collected by filtration. The filtrate was extracted with ethyl acetate (1*150 mL). The combined organics were then washed with a saturated aqueous sodium chloride solution (1*100 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. The two batches of product were combined to afford 1-trityl-1H-imidazole-4-carboxylic acid (1.55 g, 95.1%.) as a white solid: LR-MS for C23H18N2O2 (M+H)+ at m/z=355.
95.1% Stage #1: methyl 1-(triphenylmethyl)-1H-imidazole-4-carboxylate With sodium hydroxide; water In methanol at 25 - 50℃; for 19.5h; Stage #2: With hydrogenchloride In methanol; water at 25℃; 67.2 Step 2: Preparation of 1-trityl-1H-imidazole-4-carboxylic acid A solution of [L-TRITYL-LH-IMIDAZOLE-4-CARBOXYLIC] acid methyl ester (1.75 g, 4.60 mmol) in methanol (50 mL) at [25 oC] was treated with a IN aqueous sodium hydroxide solution (13.8 mL, 13.8 [MMOL).] The reaction was stirred at [25 oC] for 18 h and then heated to [50 oC] for 1.5 h. At this time, the reaction was cooled to [25 oC] and diluted with water (150 mL). The aqueous layer was brought to pH=l by treatment with a IN aqueous hydrochloric acid solution and then diluted with ethyl acetate (250 mL). The resulting precipitated product was collected by filtration. The filtrate was extracted with ethyl acetate [(1] x 150 mL). The combined organics were then washed with a saturated aqueous sodium chloride solution [(1] x 100 mL), dried over magnesium sulfate, filtered, and concentrated in vacuo. The two batches of product were combined to afford [L-TRITYL-LH-IMIDAZOLE-4-CARBOXYLIC] acid (1.55 g, 95.1%.) as a white solid:
Stage #1: methyl 1-(triphenylmethyl)-1H-imidazole-4-carboxylate With sodium hydroxide In tetrahydrofuran; methanol at 20℃; for 5h; Stage #2: With hydrogenchloride In tetrahydrofuran; methanol; water 122 1-Trityl-1 H-imidazole-4-carboxylic acid Preparation 122 1-Trityl-1 H-imidazole-4-carboxylic acid Add 1N sodium hydroxide (22.8 mL, 22.8 mmol) to 1-trityl-1H-imidazole-4-carboxylic acid methyl ester (2.8 g, 7.60 mmol) in tetrahydrofuran (20 mL) and methanol (20 mL) at room temperature. Stir the reaction mixture at room temperature for 5 hrs. Acidify the reaction mixture with 5N aqueous hydrochloride to pH about 6. Filter and dry the solid to give the title compound as a white solid (2 g, 5.64 mmol).
Stage #1: methyl 1-(triphenylmethyl)-1H-imidazole-4-carboxylate With water; lithium hydroxide In methanol at 20℃; Stage #2: With hydrogenchloride In methanol; water A.41 3H-Imidazole-4-carboxylic acid methyl ester (9.86 g, 78.2 mmol) is taken up in 150 mL DCM, triethylamine (11.9 mL, 86.0 mmol) is added and the reaction mixture is stirred for 5 min. at RT. Chlorotriphenylmethane (24.0 g, 86.0 mmol) is added and the reaction mixture is stirred overnight at RT. The reaction mixture is extracted with an aqueous 5% NaHCOs solution, the organic phase is dried over MgSO4 and concentrated under reduced pressure. The residue (20.7 g) is taken up in 100 rnL MeOH, a solution of lithium hydroxide (4.80 g, 24.0 mmol) in 20 rnL water is added drop wise and the reaction mixture is stirred over weekend at RT. The reaction mixture is acidified to pH 4 with 6N hydrochloric acid, 200 mL DCM is added and the two phase mixture is stirred vigorously. The phases are separated and the organic phase is dried over MgSO4 and concentrated under reduced pressure. Yield: 19.2 g. HPLC-MS: double peak tR = 2.55/2.67 min, (M-H)" = 353.

  • 4
  • hydrochloric acid salt of N-[6-amino-1-butyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-2-(4-amino-phenyl)-acetamide [ No CAS ]
  • [ 191103-80-7 ]
  • [ 637335-79-6 ]
YieldReaction ConditionsOperation in experiment
100% Stage #1: 1H-1-triphenylmethylimidazole-4-carboxylic acid With O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; 1-hydroxybenzotriazol-hydrate In DMF (N,N-dimethyl-formamide) at 25℃; Stage #2: hydrochloric acid salt of N-[6-amino-1-butyl-3-(2-fluoro-benzyl)-2,4-dioxo-1,2,3,4-tetrahydro-pyrimidin-5-yl]-2-(4-amino-phenyl)-acetamide With N-ethyl-N,N-diisopropylamine In DMF (N,N-dimethyl-formamide) at 0 - 25℃; for 5h; 67.3 Step 3: Preparation of [L-TRITYL-LH-IMIDAZOLE-4-CARBOXYLIC] acid [(4-[6-AMINO-1-BUTYL-] 3- (2-fluoro-benzyl)-2, 4-dioxo-1,2, 3, 4-tetrahydro-pyrimidin-5-ylcarbamoyl]-methyl}- phenyl)-amide A solution of [1-TRITYL-LH-IMIDAZOLE-4-CARBOXYLIC] acid (67 mg, 0.19 mmol) in [N, N] [DIMETHYLFORMAMIDE] (1.0 mL) at [25 oC] was treated with [1-HYDROXYBENZOTRIAZOLE] hydrate (25.4 mg, 0.19 mmol) and [O-BENZOTRIAZOL-L-YL-N, N. NTNT-TETRAMETHYLURONIUM] hexafluorophosphate (71 mg, [0.] 19 mmol). This solution was cooled to [0 oC] and then was treated with N-[6-amino-1-butyl-3-(2-fluoro-benzyl)-2, 4-dioxo-1, 2,3, 4-tetrahydro- pyrimidin-5-yl]-2- (4-amino-phenyl)-acetamide hydrochloride salt (81.5 mg, 0.17 mmol) and N, N-diisopropylethylamine (0.15 mL, 0.85 mmol). The reaction was stirred at [0 oC] for 1 h and then at [25 oC] for 4 h. At this time, the reaction was concentrated in vacuo. The residue was dissolved in ethyl acetate (100 mL) and was washed with a saturated aqueous sodium bicarbonate solution (1 x 25 mL). Some residual solids were then removed by filtration. The filtrate was washed with a saturated aqueous sodium chloride solution. The organics were dried over magnesium sulfate, filtered, and concentrated in vacuo to afford [L-TRITYL-LH-IMIDAZOLE-4-] [CARBOXYLIC ACID (4- { [6-AMINO-1-BUTYL-3-(2-FLUORO-BENZYL)-2, 4-DIOXO-1,] 2,3, 4- [TETRAHYDRO-PYRIMIDIN-5-YLCARBAMOYL]-METHYL}-PHENYL)-AMIDE] (147 mg, quant. ) as a pale yellow foam
  • 5
  • [ 857478-30-9 ]
  • H-Asn(Trt)-Lys(Boc)-Aib-Thr(Bu<SUP>t</SUP>)-Arg(Pbf)-Gln(Trt)-Arg(Pbf)-Cha-Sieber Amide resin [ No CAS ]
  • Fmoc-D-Hyp [ No CAS ]
  • Fmoc-Ser(OtBu)-OH [ No CAS ]
  • (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4,4-dimethylpentanoic acid [ No CAS ]
  • [ 135673-97-1 ]
  • [ 169555-95-7 ]
  • [ 191103-80-7 ]
  • 4-Imidazolecarbonyl-Ser-D-Hyp-Iva-Pya(4)-Cha-Leu(Me)-Asn-Lys-Aib-Thr-Arg-Gln-Arg-Cha-NH2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
303.2 mg Example 31] (Synthesis method AE): Production of 4-Imidazolecarbonyl-[D-Hyp24,Iva25,Pya(4)26,Cha27,36,Leu(Me)28,Lys30,Aib31]-PYY(23-36) (compound No. 336) Compound No. 336: (0342) Synthesis of 4-imidazolecarbonyl-[D-Hyp24,Iva25,Pya(4)26,Cha27,36,Leu(Me)28, Lys30,Aib31]-PYY(23-36) (0343) H-Asn (Trt) -Lys (Boc) -Aib-Thr(But) -Arg (Pbf) -Gln(Trt)-Arg(Pbf)-Cha-Sieber Amide resin (1.795 g, 0.5 mmol) obtained in Example 20 was weighed and placed in a reaction vessel, washed with DMF, and stirred in DMF for 20 min to swell the resin. Then, the resin was treated with Fmoc-Leu(Me)-OH (734.8 mg, 2 mmol), 0.5 M HOAt/DMF solution (4 mL, 2 mmol), DIPCDI (0.318 mL, 2 mmol) for 120 min to introduce Leu(Me) residue. The N-terminal Fmoc group was removed by 20% piperidine/DMF treatment. By a similar procedure, Cha was introduced. In the same manner, removal of Fmoc group and condensation were repeated to introduce Pya(4), Iva. The obtained resin was washed with MeOH and dried to give H-Iva-Pya(4)-Cha-Leu(Me)-Asn(Trt)-Lys(Boc)-Aib-Thr(But)-Arg(Pbf)-Gln(Trt)-Arg(Pbf)-Cha-Sieber Amide resin (SEQ ID NO:181) (2.1612 g). In this case, for introduction of Pya(4) residue, DIEA (348.4 muL, 2 mmol) was added to the reaction solution during condensation. The obtained resin (1.0806 g, 0.25 mmol) was washed with DMF and, after swelling, treated with Fmoc-D-Hyp-OH (353.4 mg, 1 mmol), 0.5 M HOAt/DMF solution (2 mL, 1 mmol), DIPCDI (159 muL, 1 mmol) for 15 hr to introduce D-Hyp. Fmoc group was removed, and Ser(But) was similarly introduced. After removal of Fmoc from the obtained Fmoc-Ser(But)-D-Hyp-Iva-Pya(4)-Cha-Leu(Me)-Asn(Trt)-Lys(Boc)-Aib-Thr (But) -Arg (Pbf) -Gln (Trt) -Arg (Pbf) -Cha-Sieber amide resin, the resin was treated with 1-trityl-1H-imidazole-4-carboxylic acid (354.4 mg, 1 mmol), DIPCDI (159 muL, 1 mmol) in DMSO (1 mL), 0.5 M HOAt/DMF solution (2 mL, 1 mmol) for 120 min, and the resin was washed and dried. The obtained resin (1.2067 g) was treated with TFA: thioanisole: m-cresol: H2O: EDT: TIS (80:5:5:5:2.5:2.5) (6 mL) for 120 min, an operation to add diethyl ether to the reaction solution, precipitate a white powder by centrifugation, and remove diethyl ether by decantation was repeated twice. The residue was dissolved in aqueous acetic acid solution, passed through a disc filter with a pore diameter 0.45 mum to remove fine granules, and concentrated in an evaporator. After confirmation of the purity of the obtained crude peptide solution by HPLC, the peptide was purified by preparative HPLC in 6 portions using Daisopak-SP100-5-ODS-P 2×25 cm, and Solution A: 0.1% TFA-water, Solution B: 0.1% TFA-containing acetonitrile, flow rate 8 mL/min, A/B: 74/26-64/36 linear concentration gradient elution (60 min) was performed. The eluted object product was fractionated in test tubes, and each fraction was analyzed by HPLC to specify fractions containing only the object product. They were combined and freeze-dried to give 365.5 mg of a white powder. (0344) The obtained purified sample (365.5 mg, 196.38 mumol) was dissolved in water (30 mL), and AG 1x8 AcO resin (4.09 mL, 4.91 mmol equivalents) was added. The solution was stood for 1 hr while occasionally stirring with hand, passed through a disc filter with a pore diameter 0.45 mum to remove fine granules, concentrated in an evaporator to reduce the liquid amount to about 5 mL, and the solution was freeze-dried by cooling in a dry ice bath to give 303.2 mg of a white powder. MALDI-TOF-MS analysis, (M+H)1860.9 (Calculated 1861.1) HPLC elution time: 9.9 min elution condition (HPLC mode d): column: Merck Chromolith Performance RP-18e(4.6×100 mm I.D.) eluent: using Solution A: 0.1% TFA-water, Solution B: 0.1% TFA-containing acetonitrile, A/B: 80/20 - 30/70 linear concentration gradient elution (25 min) flow rate: 1.0 mL/min
  • 6
  • [ 53525-60-3 ]
  • [ 191103-80-7 ]
YieldReaction ConditionsOperation in experiment
112 g With methanol; sodium hydroxide; In tetrahydrofuran; at 10 - 20℃; for 5h; Add 600 mL Methanol and 650 ml tetrahydrofuran to a 5 L dried four-mouth bottle equipped with a mechanical stirring and a thermometer, then add 125 g (0.327mol, 1.0 eq) 1-trityl -1H-imidazole-4-ethyl formate; stir to form a suspension; 1 L sodium hydroxide solution (2M, 6 eq) is dropped into the suspension, wherein the temperature is controlled to be 1020 C. Stir for 5 hrs and then the reaction ends. 1 L Hydrochloric acid solution (2M) is slowly dropped and a great amount of white solids are generated when the mixed solution is stirred. Adjust pH value to 56. Filter and dry to obtain 112 g 1-trityl-1H-imidazole-4-formic acid, with a yield of 96% and a purity of 97% (HPLC).
  • 7
  • [ 857478-30-9 ]
  • C117H157N18O19PolS2 [ No CAS ]
  • [ 71989-33-8 ]
  • (S)-2-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-4,4-dimethylpentanoic acid [ No CAS ]
  • [ 135673-97-1 ]
  • [ 169555-95-7 ]
  • [ 191103-80-7 ]
  • [ 139262-20-7 ]
  • 4-Imidazolecarbonyl-Ser-D-Hyp-Iva-Pya(4)-Cha-Leu(Me)-Asn-Lys-Aib-Thr-Arg-Gln-Arg-Cha-NH2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
All peptides were synthesized in the same manner following thesynthesis procedure for 4-imidazolecarbonyl-[D-Hyp24,Iva25,Pya(4)26,Cha27,36,cMeLeu28,Lys30,Aib31]PYY(23-36) (31). Using a commerciallyavailable Sieber amide resin (391 mg, 0.25 mmol) as astarting material and the ABI 433A peptide synthesizer (DCC/HOBt0.25-mmol protocol), amino acids were successively condensed togive H-Asn(Trt)-Lys(Boc)-Aib-Thr(tBu)-Arg(Pbf)-Gln(Trt)-Arg(Pbf)-Cha-NH-Sieber Amide Resin (903 mg, 0.289 mmol/g). A 34.6-mg(0.01 mmol) aliquot of the obtained resin was weighed, washedwith DMF, and after swelling, treated with Fmoc-cMeLeu-OH(18.4 mg, 0.05 mmol), DIPCDI (8.0 lL, 0.05 mmol), and 0.5 MHOAt/DMF (0.1 mL, 0.05 mmol) in DMF for 90 min to introducecMeLeu residue on position 28. The resin was treated with 20%piperidine/DMF to remove N-terminal Fmoc group, then Cha wasintroduced on position 27 in the same manner. Pya(4), Iva,D-Hyp, Ser(tBu) and N-terminal 1-trityl-1H-imidazole-4-carboxylicacid were introduced by repeating the same steps. The resin waswashed with DMF, methanol, and dried to give 1-trityl-1Himidazole-4-carbonyl-Ser(tBu)-D-Hyp-Iva-Pya(4)-Cha-cMeLeu-Asn(Trt)-Lys(Boc)-Aib-Thr(tBu)-Arg(Pbf)-Gln(Trt)-Arg(Pbf)-Cha-Sieberamide resin (43.0 mg, 0.01 mmol). Trifluoroacetic acid (TFA):thioanisole:m-cresol:H2O:1,2-ethanedithiol:triisopropylsilane (80:5:5:5:2.5:2.5) (0.4 mL) was added to the entire amount of the obtainedresin, then the mixture was stirred at ambient temperature for90 min, and diethyl ether was added to the reaction solution to allowprecipitation of a white powder. Diethyl ether was removed bydecantation after centrifugation of the suspension, and the procedurewas repeated to remove acid and the scavenger. The residuewas extracted with an aqueous acetic acid solution and purified bypreparative HPLC using a Daisopak-SP100-5-ODS-P column(250 20mmi.d.) to give 5.1 mgof a white powder. Mass spectrum:MALDI-TOF (a-cyano-4-hydroxycinnaminic acid, monoisotopic) [M+H]+ 1861.25 (calcd. 1861.09). Elution time on RP-HPLC: 6.43 min.Elution conditions: a Phenomenex Kinetex XB-C18 column(1.7 mm, 100 2.1 mm i.d.), linear density-gradient elution witheluents A/B = 95/5-45/55 (10 min) using 0.1% TFA in water as eluentA and 0.1% TFA-containing acetonitrile as eluent B; flow rate:0.5 mL/min.
  • 8
  • [ 857478-30-9 ]
  • [ 1231709-22-0 ]
  • C117H157N18O19PolS2 [ No CAS ]
  • [ 71989-33-8 ]
  • [ 135673-97-1 ]
  • [ 169555-95-7 ]
  • [ 191103-80-7 ]
  • [ 139262-20-7 ]
  • 4-Imidazolecarbonyl-Ser-D-Hyp-Iva-Pya(4)-Cha-Iva-Asn-Lys-Aib-Thr-Arg-Gln-Arg-,Cha-NH2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: All peptides were synthesized in the same manner following thesynthesis procedure for 4-imidazolecarbonyl-[D-Hyp24,Iva25,Pya(4)26,Cha27,36,cMeLeu28,Lys30,Aib31]PYY(23-36) (31). Using a commerciallyavailable Sieber amide resin (391 mg, 0.25 mmol) as astarting material and the ABI 433A peptide synthesizer (DCC/HOBt0.25-mmol protocol), amino acids were successively condensed togive H-Asn(Trt)-Lys(Boc)-Aib-Thr(tBu)-Arg(Pbf)-Gln(Trt)-Arg(Pbf)-Cha-NH-Sieber Amide Resin (903 mg, 0.289 mmol/g). A 34.6-mg(0.01 mmol) aliquot of the obtained resin was weighed, washedwith DMF, and after swelling, treated with Fmoc-cMeLeu-OH(18.4 mg, 0.05 mmol), DIPCDI (8.0 lL, 0.05 mmol), and 0.5 MHOAt/DMF (0.1 mL, 0.05 mmol) in DMF for 90 min to introducecMeLeu residue on position 28. The resin was treated with 20%piperidine/DMF to remove N-terminal Fmoc group, then Cha wasintroduced on position 27 in the same manner. Pya(4), Iva,D-Hyp, Ser(tBu) and N-terminal 1-trityl-1H-imidazole-4-carboxylicacid were introduced by repeating the same steps. The resin waswashed with DMF, methanol, and dried to give 1-trityl-1Himidazole-4-carbonyl-Ser(tBu)-D-Hyp-Iva-Pya(4)-Cha-cMeLeu-Asn(Trt)-Lys(Boc)-Aib-Thr(tBu)-Arg(Pbf)-Gln(Trt)-Arg(Pbf)-Cha-Sieberamide resin (43.0 mg, 0.01 mmol). Trifluoroacetic acid (TFA):thioanisole:m-cresol:H2O:1,2-ethanedithiol:triisopropylsilane (80:5:5:5:2.5:2.5) (0.4 mL) was added to the entire amount of the obtainedresin, then the mixture was stirred at ambient temperature for90 min, and diethyl ether was added to the reaction solution to allowprecipitation of a white powder. Diethyl ether was removed bydecantation after centrifugation of the suspension, and the procedurewas repeated to remove acid and the scavenger. The residuewas extracted with an aqueous acetic acid solution and purified bypreparative HPLC using a Daisopak-SP100-5-ODS-P column(250 20mmi.d.) to give 5.1 mgof a white powder. Mass spectrum:MALDI-TOF (a-cyano-4-hydroxycinnaminic acid, monoisotopic) [M+H]+ 1861.25 (calcd. 1861.09). Elution time on RP-HPLC: 6.43 min.Elution conditions: a Phenomenex Kinetex XB-C18 column(1.7 mm, 100 2.1 mm i.d.), linear density-gradient elution witheluents A/B = 95/5-45/55 (10 min) using 0.1% TFA in water as eluentA and 0.1% TFA-containing acetonitrile as eluent B; flow rate:0.5 mL/min.
  • 9
  • [ 857478-30-9 ]
  • C117H157N18O19PolS2 [ No CAS ]
  • [ 71989-33-8 ]
  • [ 94744-50-0 ]
  • [ 135673-97-1 ]
  • [ 169555-95-7 ]
  • [ 191103-80-7 ]
  • [ 139262-20-7 ]
  • 4-Imidazolecarbonyl-Ser-D-Hyp-Iva-Pya(4)-Cha-Aib-Asn-Lys-Aib-Thr-Arg-Gln-Arg-Cha-NH2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: All peptides were synthesized in the same manner following thesynthesis procedure for 4-imidazolecarbonyl-[D-Hyp24,Iva25,Pya(4)26,Cha27,36,cMeLeu28,Lys30,Aib31]PYY(23-36) (31). Using a commerciallyavailable Sieber amide resin (391 mg, 0.25 mmol) as astarting material and the ABI 433A peptide synthesizer (DCC/HOBt0.25-mmol protocol), amino acids were successively condensed togive H-Asn(Trt)-Lys(Boc)-Aib-Thr(tBu)-Arg(Pbf)-Gln(Trt)-Arg(Pbf)-Cha-NH-Sieber Amide Resin (903 mg, 0.289 mmol/g). A 34.6-mg(0.01 mmol) aliquot of the obtained resin was weighed, washedwith DMF, and after swelling, treated with Fmoc-cMeLeu-OH(18.4 mg, 0.05 mmol), DIPCDI (8.0 lL, 0.05 mmol), and 0.5 MHOAt/DMF (0.1 mL, 0.05 mmol) in DMF for 90 min to introducecMeLeu residue on position 28. The resin was treated with 20%piperidine/DMF to remove N-terminal Fmoc group, then Cha wasintroduced on position 27 in the same manner. Pya(4), Iva,D-Hyp, Ser(tBu) and N-terminal 1-trityl-1H-imidazole-4-carboxylicacid were introduced by repeating the same steps. The resin waswashed with DMF, methanol, and dried to give 1-trityl-1Himidazole-4-carbonyl-Ser(tBu)-D-Hyp-Iva-Pya(4)-Cha-cMeLeu-Asn(Trt)-Lys(Boc)-Aib-Thr(tBu)-Arg(Pbf)-Gln(Trt)-Arg(Pbf)-Cha-Sieberamide resin (43.0 mg, 0.01 mmol). Trifluoroacetic acid (TFA):thioanisole:m-cresol:H2O:1,2-ethanedithiol:triisopropylsilane (80:5:5:5:2.5:2.5) (0.4 mL) was added to the entire amount of the obtainedresin, then the mixture was stirred at ambient temperature for90 min, and diethyl ether was added to the reaction solution to allowprecipitation of a white powder. Diethyl ether was removed bydecantation after centrifugation of the suspension, and the procedurewas repeated to remove acid and the scavenger. The residuewas extracted with an aqueous acetic acid solution and purified bypreparative HPLC using a Daisopak-SP100-5-ODS-P column(250 20mmi.d.) to give 5.1 mgof a white powder. Mass spectrum:MALDI-TOF (a-cyano-4-hydroxycinnaminic acid, monoisotopic) [M+H]+ 1861.25 (calcd. 1861.09). Elution time on RP-HPLC: 6.43 min.Elution conditions: a Phenomenex Kinetex XB-C18 column(1.7 mm, 100 2.1 mm i.d.), linear density-gradient elution witheluents A/B = 95/5-45/55 (10 min) using 0.1% TFA in water as eluentA and 0.1% TFA-containing acetonitrile as eluent B; flow rate:0.5 mL/min.
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