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CAS No. : | 162558-25-0 | MDL No. : | MFCD00235896 |
Formula : | C23H26N2O6 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | PKAUMAVONPSDRW-IBGZPJMESA-N |
M.W : | 426.46 | Pubchem ID : | 2756103 |
Synonyms : |
|
Num. heavy atoms : | 31 |
Num. arom. heavy atoms : | 12 |
Fraction Csp3 : | 0.35 |
Num. rotatable bonds : | 11 |
Num. H-bond acceptors : | 6.0 |
Num. H-bond donors : | 3.0 |
Molar Refractivity : | 113.72 |
TPSA : | 113.96 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | Yes |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | Yes |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | Yes |
Log Kp (skin permeation) : | -6.49 cm/s |
Log Po/w (iLOGP) : | 2.66 |
Log Po/w (XLOGP3) : | 3.39 |
Log Po/w (WLOGP) : | 3.5 |
Log Po/w (MLOGP) : | 2.18 |
Log Po/w (SILICOS-IT) : | 2.56 |
Consensus Log Po/w : | 2.86 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 1.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -4.18 |
Solubility : | 0.0282 mg/ml ; 0.000066 mol/l |
Class : | Moderately soluble |
Log S (Ali) : | -5.46 |
Solubility : | 0.00147 mg/ml ; 0.00000345 mol/l |
Class : | Moderately soluble |
Log S (SILICOS-IT) : | -5.78 |
Solubility : | 0.000711 mg/ml ; 0.00000167 mol/l |
Class : | Moderately soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 2.0 |
Synthetic accessibility : | 4.32 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H332-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 |
---|---|---|
67% | With sodium hydrogencarbonate In tetrahydrofuran; water at 0 - 20℃; for 16 h; | To a (25)-3-amino-2-[{9H-fluoren-9yl-methanol}amino]propanoic acid as hydrochloride salt (15 g, 41.3 mmoles) in a 1: 1 mixture of water (150 mL) and tetrahydrofuran (150 ml) was added solid sodium bicarbonate (6.95g, 82.7 mmol) at 0°C under stirring. Boc anhydride (10.82 g, 49.6 mmol) was added drop-wise to it. The reaction mixture was allowed to warm to room temperature and stirred for 16 hours. The reaction mixture was extracted with 250 ml of diethyl ether. The aqueous layer was acidified to pH of 1 by addition of 5percent potassium hydrogen sulphate solution followed by extraction with 2 x 250 ml ethyl acetate and 250 ml dichloromethane. The combined extracts were dried over anhydrous sodium sulphate and the solvent evaporated under reduced pressure to obtain the 13.08 g of titled product, as a white solid in 67percent yield. Analysis:Mass: 427.3 (M+1); for Molecular Formula of C23H26N206 and for Molecular Weight of 426. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; trifluoro-[1,3,5]triazine; In dichloromethane; | 1. Preparation of compound B. To a stirred solution of the acid (A) (1.69g, 3.97 mmole) in CH2Cl2 (5 mL) was added pyridine (32 uL, 3.97 mmole) and cyanuric fluoride (669 uL, 7.93 mmole). The reaction was stirred overnight and water (10 mL) was added. The mixture was extracted with CH2Cl2 (15 mL x 2). The organic layer was dried (Na2SO4) and solvent removed in vacuo. The resulting acid fluoride was dissolved in CH2Cl2 (5 mL). To this solution was added triethylamine (732 uL, 5.25 mmole) and 3-amino-methylpyridine (428 uL, 4.2 mmole). The mixture was stirred for 3 hours and then diluted with CH2Cl2 (10 mL). the solution was washed with sat. NH4Clsolution (5 mL). The organic layer was dried (Na2SO4) and solvent was removed in vacuo. The residue was purified by flash column chromatography with 2percent MeOH in CH2Cl2 to give 1.4g desired product in 68percent yield. MS: m/z 517 (MH+). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; 1-ethyl-(3-(3-dimethylamino)propyl)-carbodiimide hydrochloride; In N,N-dimethyl-formamide; at 20℃; for 16h; | Synthesis Example 61-1: Synthesis of (S)-2-(N-Fmoc amino)-3-(N-Boc amino) propionate 1-naphthalenemethylamide (Compound X-4) 201.6 mg of commercially available (S)-2-(N-Fmoc amino)-4-(N-Boc amino) propionate was dissolved in 2.0 ml of DMF, and then 110.0 mg of WSCI hydrochloride and 75.6 mg of HOBt were added and dissolved therein. Then, 29 mul of 1-naphthalene methylamine was added to the solution and the whole was stirred for 16 hours at room temperature. On completion of the reaction, the solvent was distilled off. The residue was purified by means of silica gel column chromatography (10 g, chloroform/methanol = 30/1), and 226.3 mg of the above-mentioned compound was obtained as a white solid product. MS(FAB,Pos.):m/z=566[M+1]+ 1H-NMR(500MHz,DMSO-d6):delta=1.37(9H,s),3.26-3.29(2H,m),4.10-4.25 (2H,m),4.27-4.29(2H,m),4.76(2H,d,J=5.6Hz),6.80(1H,t,J=5.6Hz),7.30-7.37(2H,m),7.43(2H,t,J=7.3Hz),7.44(2H,d,J=5.8Hz),7.71(2H, d,J=7.7Hz),7.88(1H,t,J=4.3Hz),7.90(2H,d,J=7.6Hz),7.93(1H,m),8.03(1H,d,J=6.8Hz),8.51(1H,t,J=5.6Hz). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
The protected amino acids were introduced in the following order:Fmoc-Thr(But)-OH, Fmoc-Dbu(Boc)-OH, Fmoc-Val-OH, Fmoc-Lys(Z)-OH, Fmoc-D-Trp-OH, Fmoc-Tyr(But)-OH, Fmoc-Glu(OBut)-OH, Fmoc-D-Nal-OH. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Synthesis of compound 10 [] 10 was obtained according to the standard solid-phase synthesis protocol. The amino acids Fmoc-Dpr(Boc)-OH, Fmoc-Dpr(Fmoc)-OH, Fmoc-Dpr(Fmoc)-OH, Fmoc-Ado-OH, and Fmoc-Dpr(Fmoc)-OH were coupled to TentaGel Sieber amide resin. After final finoc removal the resin was agitated with 5 eq maleimidopropionic acid and 5 eq DIC in relation to amino groups in DMF for 30 min. 10 was cleaved from resin with TFA/TES/water 95/3/2 (v/v/v). After evaporation of solvent, product 10 was purified by RP-HPLC. MS: [M+H]+ = 2494.6 (MW calculated = 2495.4 g/mol) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Preparation of Fmoc-Dap(Boc)-NHOH on hydroxylamine 2-chlorotrityl resin (2). A suspension of N-Fmoc-hydroxylamine 2-chlorotrityl resin (1) (3.288 g,2.53 mmol, 0.77 mmol/g, Novabiochem) in DCM (40 mL) was shaken for 2 h and drained. The resin was treated with 20percent piperidine in DMF (40 mL) for 1 hour, washed with DMF(2x40 mL), treated a second time with 20percent piperidine in DMF (40 mL), washed with DMF(3x40 mL) and DCM (3x40 mL) and drained completely. In a separate flask, Fmoc-Dap(Boc)-OH (3.175 g, 7.44 mmol), HATU (2.829 g, 7.44 mmol) and DIEA (4.3 mL, 24.7 mmol) were dissolved in DMF (35 mL), stirred three minutes and added to the resin. After shaking for 48 h, the mixture was drained, washed with DMF (4x40 mL) and DCM (4x40 mL) and dried in vacuo to give 3.530 g of (2) as a yellow resin. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethylmorpholine;; O-<[cyano(ethoxycarbonyl)methylene]amino>-1,1,3,3-tetramethyluronium tetrafluoroborate; In N,N-dimethyl-formamide; at 0℃; for 1h; | Example 87: 4-[(S)-3-Acetylamino-2-({5-[2-((S)-2-cyclobutylcarbamoyl-pyrrolidin-1 - yl)-2-oxo-ethoxy]-1 -phenyl-1 H-pyrazole-3-carbonyl}-amino)-propionyl]-piperazine-1 - carboxylic acid ethyl ester; i) 4-[(S)-3-tert-Butoxycarbonylamino-2-(9H-fluoren-9-ylmethoxycarbonylamino)- propionyl]-piperazine-1 -carboxylic acid ethyl ester; To a solution of 0.86 ml 1-ethoxycarbonylpiperazine, 0.83 ml N-ethylmorpholine and 2.50 g N-alpha-Fmoc-N-beta-Boc-L-diaminopropionic acid in 50 ml DMF were added 1.92 g TOTU at 0 °C. After 1 h the reaction mixture was diluted with 100 ml ethyl acetate and subsequently extracted with aqueous LiCI (4 percent), half-saturated aqueous NaHCO3 and water. The crude product obtained after evaporation of the solvent was used in the subsequent reaction. Yield: 3.3 g colorless foam. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | General procedure: The glycopeptide was assembled manually by using a fritted glass reaction vessel according to a standard Fmoc SPPS protocol. Fmoc-Ala-Wang resin was swollen in DMF (4 mL) for 2 h before the synthesis and then deprotected with 20percent piperidine solution in DMF (2 .x. 15 min). The next Fmoc-protected amino acid (4 equiv), HBTU (3.6 equiv) and HOBt (4 equiv) were dissolved in DMF (3 mL), it was shaken for 5 min, then DIPEA (4 equiv) was added and this mixture shaken for another 2 min before it was transferred to the reaction vessel which contained the resin. The reaction mixture was shaken for 4 h or overnight at rt, filtered and washed with DMF (5 .x. 5 mL). For diaminopropionic acid coupling, Fmoc-Dpr(Boc)-OH (2 equiv) and HATU (2 equiv) were dissolved in DMF (3 mL), shaken for 5 min and then DIPEA (2 equiv) was added. This mixture was shaken for another 2 min and then transferred to the reaction vessel. The reaction mixture was shaken overnight at rt, filtered and washed with DMF (5 .x. 5 mL). Any unreacted amino groups are capped as acetamides by treatment of the resin with a solution of Ac2O (160 muL) and DIPEA (280 muL) in 3 mL DMF (1 .x. 60 min, 1 .x. 30 min). After coupling of the N-terminal amino acid, the peptide was treated first with piperidine to remove the terminal Fmoc-group and capped afterwards. Cleavage of the peptide from the resin was achieved with TFA/CH2Cl2 (5:1) (1 .x. 15 min, 1 .x. 10 min), followed by washing with EtOH. The solvent was removed in vacuo and the crude product subjected to lyophilization in order to yield a fluffy product, which can be easily handled. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
30 mg; 42 mg | Example 19:Synthesis of linker building blocks 17a and 17bExample 19: Synthesis of linker building blocks 17a and 17b Linker building blocks 17a and 17b were synthesized according to the following scheme: fmoc O 17a and 17b L-Fmoc-Dpr(Boc)-OH (100 mg, 0.234 mmol) was dissolved in 0.5 mL DMF (anhydrous, mol. sieve). 6-(5'-Tritylsulfanyl)-hexaneamine (71 mg, 0.189 mmol), COMU (97 mg, 0.227 mmol) and DIPEA (66 mu, 0.378 mmol) were added and mixture was stirred for 1 h at RT. Piperidine (50 mu, 0.505 mmol) and DBU (40 mu, 0.336 mmol) were added and stirring was continued for 10 h. cz's-Cyclohexanedicarboxylic anhydride (600 mg, 3.89 mmol) was added and stirring was continued for 1 h. Solution was quenched with water/acetonitrile and acidified with acetic acid Building blocks were purified by RP-HPLC. Structures assignment of the earlier eluting diastereomer 17a and the later eluting diastereomer 17b was done arbitrarily and could also be reverse. Yield: 17a 30 mg (0.042 mmol), 17b 42 mg (0.059 mmol) MS: m/z 716.2 = [M+Hf (MW calculated = 716.0 g/mol). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 1h; | Example 19: Synthesis of linker building blocks 17a and 17b Linker building blocks 17a and 17b were synthesized according to the following scheme: fmoc O 17a and 17b L-Fmoc-Dpr(Boc)-OH (100 mg, 0.234 mmol) was dissolved in 0.5 mL DMF (anhydrous, mol. sieve). 6-(5'-Tritylsulfanyl)-hexaneamine (71 mg, 0.189 mmol), COMU (97 mg, 0.227 mmol) and DIPEA (66 mu, 0.378 mmol) were added and mixture was stirred for 1 h at RT. Piperidine (50 mu, 0.505 mmol) and DBU (40 mu, 0.336 mmol) were added and stirring was continued for 10 h. cz's-Cyclohexanedicarboxylic anhydride (600 mg, 3.89 mmol) was added and stirring was continued for 1 h. Solution was quenched with water/acetonitrile and acidified with acetic acid Building blocks were purified by RP-HPLC. Structures assignment of the earlier eluting diastereomer 17a and the later eluting diastereomer 17b was done arbitrarily and could also be reverse. Yield: 17a 30 mg (0.042 mmol), 17b 42 mg (0.059 mmol) MS: m/z 716.2 = [M+H]+ (MW calculated = 716.0 g/mol). | |
With 1-[(1-(cyano-?2-?ethoxy-?2-?oxoethylidenaminooxy)?dimethylamino-?morpholino)]-uronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 20℃; for 1h;Molecular sieve; | L-Fmoc-Dpr(Boc)-OH (100 mg, 0.234 mmol) was dissolved in 0.5 mL DMF (anhydrous, mol. sieve). 6-(5'-Tritylsulfanyl)-hexaneamine (71 mg, 0.189 mmol), COMU (97 mg, 0.227 mmol) and DIPEA (66 mu, 0.378 mmol) were added and mixture was stirred for 1 h at RT. Piperidine (50 mu, 0.505 mmol) and DBU (40 mu, 0.336 mmol) were added and stirring was continued for 10 h. cz's-Cyclohexanedicarboxylic anhydride (600 mg, 3.89 mmol) was added and stirring was continued for 1 h. Solution was quenched with water/acetonitrile and acidified with acetic acid. Building blocks were purified by RP-HPLC. Structures assignment of the earlier eluting diastereomer 4a and the later eluting diastereomer 4b was done arbitrarily and could also be reverse. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With C97H127Cl2N29O11Pt; benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; In N,N-dimethyl-formamide; at 37℃; | Synthesis of 2H-5-CA-Biotin and 2P-5-CA-Biotin (Scheme S5). 2H-5-CA-Biotin was synthesized as described previously.616 The peptoid scaffold, 2P-5, was synthesized as previously described on Rink amide resin.616 To the 2P-5 resin (100 mg, 0.059 mmoles) was added a mixture of Fmoc-Dap(Boc)-OH (0.59 mmoles), HOBT (0.59 mmoles), HBTU (0.59 mmoles), and DIPEA (0.3 mL) in 2 mL of DMF. The reaction was incubated overnight at 37 °C with shaking. The solution was removed and the resin was washed with DMF (3 x 5 mL) to afford resin-bound 2P-5-Fmoc-Dap(Boc). The Fmoc-protecting group was removed by treating the resin with 20percent piperidine in DMF at room temperature for 20 min, affording 2P-4-Dap(Boc)-NH2. To the 2P-5-Dap(Boc)-NH2-containing resin was added biotin (0.2 mmol, 3.3 eq.), 0.3 mmol HOBT, and 0.3 mmol HBTU, and DIPEA (0.3 mL) dissolved in 2 mL of DMF. The reaction was shaken at 37 °C for 4 h to afford 2P-5-Dap(Boc)-Biotin (resin-bound). After washing the resin with DMF three times, Ht-N3 (synthesized as previously described)617 (61 muiotaetaomicron, 5 eq.) in DMF was added to the resin to afford 2H-5-Dap(Boc)-Biotin via a click reaction.618'619 2H-5- Dap(Boc)-Biotin was cleaved from resin using a solution of 60percent (v/v) trifluoroacetic acid (TFA), 30percent (v/v) DCM, and 10percent (v/v) H20. The solvent was removed under a stream of air, and the product (2H-5-Dap-Biotin) was purified on a Waters 1525 binary HPLC pump equipped with a Waters 2487 dual absorbance detector system and a SunFire? Prep C18 OBD? 5 D5 19x150 mm column. Product was eluted using a linear gradient starting from 80percent solvent A (H20 + 0.1 percent (v/v) TFA) and 20percent solvent B (MeOH+ 0.1 percent (v/v) TFA) to 0percent A and 100percent B over 60 min and a flow rate of 5 mL/min |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; O-(1H-benzotriazol-1-yl)-N,N,N',N'-tetramethyluronium hexafluorophosphate; N-ethyl-N,N-diisopropylamine; In N,N-dimethyl-formamide; at 37℃; | Synthesis of 2H-4-CA-Biotin (Scheme S3). The 2P-4 peptoid was synthesized as described above. To the 2P-4 resin (100 mg) was added Fmoc-Dap(Boc)-OH (0.5 M in 1 mL DMF containing 0.5 M HOBT and 0.5 M HBTU) followed by DIPEA (0.2 mL). The reaction was shaken overnight at 37 °C. The solution was removed, and the resin was washed with DMF (3 x 5 mL), affording resin- bound 2P-4-Fmoc-Dap(Boc). The Fmoc-protecting group was removed by treating the resin with 20percent piperidine in DMF at room temperature for 20 min, affording 2P-4-Dap(Boc)-NH2. To the 2P-4-Dap(Boc)-NH2-containing resin was added biotin (0.2 mmol in 1 mL DMF (3.3 eq.) containing 0.3 mmol HOBT and 0.3 mmol HBTU) followed by DIPEA (0.2 mL). The reaction was shaken at 37 °C for 4 h to afford 2P-4-Dap(Boc)-Biotin (resin-bound). Ht-N3 was then clicked with 2P-4-Dap(Boc) as previously decribed to produce 2H-4-Dap(Boc)- Biotin.61 64 2H-4-Dap(Boc)-Biotin was de-protected and cleaved from resin using a solution of 95percent TFA (v/v), 2.5percent (v/v) H20 and 2.5percent (v/v) diisopropylsilane. The solvent was removed under a stream of air, and the product (2H-4-Dap-Biotin) was purified by HPLC as described above. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: Example 1The following amino acids were used: Fmoc-Gly-OH, Fmoc-Leu-OH, Fmoc-Pro-OH, Fmoc- Dap(Boc)-OH, Fmoc-Asn(Trt)-OH, Fmoc-Gln(Trt)-OH, Fmoc-Ile-OH, Fmoc-Tyr(tBu)-OH and mono-tBu succinate. MS (M+H+): expected 971.1; observed 971.2Peptide Synthesis:The peptide was synthesized using CEM Microwave technology with coupling times of 5 minutes per amino acid at elevated temperature (78 °C) and a 0.25mmol scale. The synthesis is carried out using the TentalGel-S RAM resin as a solid support (0.24 meq /g). All amino acids used were dissolved in DMF to 0.2 mol concentration. A mixture of HOBT/HBTU 1: 1 (0.5 mol /L) 4 eq. and DIPEA 4eq. was used to activate the amino acids. Fmoc-Cleavage was achieved with Piperidine in DMF (20 percent) for 3 min. Fmoc-cleavage was repeated.General Synthesis Description:The cyclic peptides can be generated either via on-bead cyclisation (Allyl/Aloc strategy METHODE A) or as fully deprotected linear peptides via solution phase cyclisation (METHODE B).Linear peptides were either synthesized manually or using microwave technology via state-of- the-art solid phase synthesis protocols (Fmoc-chemistry) as referenced by e.g.: Kates and Albericio, Eds., "Solid Phase Synthesis: A practical guide", Marcel Decker, New York, Basel, 2000. As a solid support TentaGel-S-RAM resin (0.24 meq /g) was used. All Fmoc-amino acids were added in a 4-fold excess after activation with HOBT/HBTU 1 : 1 (0.5 mol/L in DMF) and 4 eq of DIPEA (2 mol/L in NMP). Fmoc-cleavage was achieved with 20percent Piperidine in DMF.Allyl/Aloc- Cleavage & Lactam- Cyclisation:(METHODE A: The resin-linked peptides were treated manually with a solution of 20 eq phenylsilane in DCM and 0.05 eq of tetrakis triphenylphosphine palladium for 30 min at RT. This procedure was repeated. The resin was washed with a solution of 0.5percent sodium dithiocarbamate in DMF. For the on-bead lactam formation, again activation reagent was added to the resin and shaken for additional 8h at RT. Completion of cyclisation was verified via Ninhydrin-test.METHODE B: Peptides were cyclized in solution after deprotection and cleavage from the resin and standard work-up. Crude peptides were treated with standard peptide activation regents in DMF. The cyclisation was monitored via HPLC.Cleavage & work-up:A cleavage-cocktail of trifluoroacetic acid, triisopropylsilane and water (95/2.5/2.5) was added to the resin and shaken for lh at RT. Cleaved peptides were precipitated in cold Ether (-18°C ). The peptides were centrifuged and the residue washed twice with cold ether. The residues were again dissolved in water/ acetonitrile and lyophilized.Purification :Peptides were purified using reversed phase high performance liquid chromatography (RP- HPLC) using a Reprospher 100 C18-T Columm (100 x 4.6 mm, 5u particle size) as a stationary phase and water/acetonitrile as eluent (0053) (Gradient 1-50 percent MeCN over 30 min). Fractions were collected and analyzed by LC/MS. Pure product samples were combined and lyophilized. All peptides were obtained as white powders with a purity >85 percent. Product identification was obtained via mass spectrometry. All standard amino acids were purchased from CEM. Fmoc-SAR-OH and Fmoc-N-Cyclopropyl- Glycine were purchased from Bachem and Enamine respectively. Mono-tBu-Succinate were purchased from Sigma- Aldrich |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Compound II was synthesized using standard fluorenylmethyloxycarbonyl (Fmoc) solid phase peptide synthesis (SPPS) starting from Fmoc-Cys(Trt)-Wang resin (Novabiochem; Catalog 04-12-2050). Compound II was purified using reverse phase preparative HPLC (Waters, xTerra Ci8 10 mupi; 19 x 250 mm) A=0.1 TFA, B=Acetonitrile (ACN); lambda^257 nm; Solvent gradient: 5percent B to 80percent B in 25 min, 80percent B wash 30 min run, (61percent). Purified compounds were analyzed using reverse phase analytical HPLC (Waters, X- Bridge Cl8 5 muetaiota; 3.0 x 15 mm); A=0.1 TFA, B=ACN; lambda^257 nm, 5percent B to 80percent B in 10 min, 80percent B wash 15 min run. C47H65N2O17S; MW=1060.13 g/mol; white solid; Rt= 7.7 min; 1H NMR (DMSO-d6/D20) delta 0.93 (m, 2H); 1.08 (m, 5H); 1.27 (m, 5H); 1.69 (m, 2H); 1.90 (m, 2H); 1.94 (m, 2H); 2.10 (m, 2H); 2.24 (q, 2H); 2.62 (m, 2H); 2.78 (m, 4H); 2.88 (dd, 1H); 2.96 (t, 2H); 3.01 (dd, 1H); 3.31 (dd, 1H); 3.62 (dd, 1H); 3.80 (q, 1H, aH ); 4.07 (m, 1H, aH); 4.37 (m, 1H, aH); 4.42 (m, 2H, aH); 4.66 (m, 1H, aH); 7.18 (m, 10H, Ar-H): LC-MS=1061 (M+H)+; ESI-MS=1061 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Compound IV was prepared according to the following scheme as taught in US patent number 7, 128,893, which is incorporated herein by reference. ir R R = = FFlmoc vi |? R' = F3CCO, R" = fBu, R'" = Boc, R"" = Trt, Y = Wang Resi R' = F3CCO, R" = H, R'" = H, R"" = H, Y = OH l? R' = H, R" = H, R'" = H, R"" = H, Y = OH "Reagents and conditions: i) 20percent Piperidine, DMF; ii)Fmoc-Asp(OiBu)-OH, PyBop, DIPEA, DMF; iii) Boc-Dap(Fmoc)-OH, PyBop, DIPEA, DMF; iv) Fmoc-D-Glu-OiBu, PyBop, DIPEA, DMF; v) N10-TFA-Pte- OH, DIPEA, DMSO; vi) F3CC02H, HSCH2CH2SH, Pr3SiH; vii) H4NOH, pH = 10.3. EC20 was prepared by a polymer-supported sequential approach using the Fmoc-strategy (see Scheme 1 below; Fmoc = 9-fluorenylmethyloxycarbonyl; Boc = tert-butyl- oxycarbonyl; Dap = diaminopropionic acid; DMF = dimethylformamide; DIPEA = diisopropyl- ethylamine). EC20 was synthesized on an acid-sensitive Wang resin loaded with Fmoc-L- Cys(Trt)-OH. Benzotriazole- l-yl-oxy-tris-pyrrolidino-phosphonium-hexafluorophosphate (PyBOP) was applied as the activating reagent to ensure efficient coupling using low equivalents of amino acids. Fmoc protecting groups were removed after every coupling step under standard conditions (20percent piperidine in DMF). After the last assembly step the peptide was cleaved from the polymeric support by treatment with 92.5percent trifluoroacetic acid containing 2.5percent ethanedithiol, 2.5percent triisopropylsilane and 2.5percent deionized water. This reaction also resulted in simultaneous removal of the t-Bu, Boc and trityl protecting groups. Finally, the trifluoroacetyl moiety was removed in aqueous ammonium hydroxide to give EC20. |
Tags: 162558-25-0 synthesis path| 162558-25-0 SDS| 162558-25-0 COA| 162558-25-0 purity| 162558-25-0 application| 162558-25-0 NMR| 162558-25-0 COA| 162558-25-0 structure
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
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P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
Sorry,this product has been discontinued.
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