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CAS No. : | 117322-30-2 | MDL No. : | MFCD01074696 |
Formula : | C21H21NO4 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | IECZEINPZOFWNU-UHFFFAOYSA-N |
M.W : | 351.40 | Pubchem ID : | 978345 |
Synonyms : |
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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 |
---|---|---|
28% | Stage #1: With sodium hydrogencarbonate In water; acetonitrile at 20℃; Stage #2: With hydrogenchloride In water; acetonitrile |
1- (((9H-Fluoren-9-yl)methoxy)carbonylamino)cyclopentanecarboxylic acid(compound 4 of example A): Fmoc-OSu (3.13 g, 9.3 mmol) was added to a solution of 1- aminocyclo- pentanecarboxylic acid (1.0 g, 7.8 mmol) and NaHC03 (1.63 g, 19.4 mmol) in acetonitrile/water (100 mL, 1 : 1). The reaction mixture was stirred at room temperature overnight. Most of the solvent was removed under reduced pressure and the resulting mixture was adjusted to pH = 2 with 2 N HCI and extracted with DCM. The combined extracts were washed with brine, dried over anhydrous Na2S04 and concentrated. The residue was purified by flash column chromatography on silica gel (PE/EA = 20: 1) to afford compound 4 of example A (0.75 g, 28percent yield) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28% | 1- (((9H-Fluoren-9-yl)methoxy)carbonylamino)cyclopentanecarboxylic acid(compound 4 of example A): Fmoc-OSu (3.13 g, 9.3 mmol) was added to a solution of 1- aminocyclo- pentanecarboxylic acid (1.0 g, 7.8 mmol) and NaHC03 (1.63 g, 19.4 mmol) in acetonitrile/water (100 mL, 1 : 1). The reaction mixture was stirred at room temperature overnight. Most of the solvent was removed under reduced pressure and the resulting mixture was adjusted to pH = 2 with 2 N HCI and extracted with DCM. The combined extracts were washed with brine, dried over anhydrous Na2S04 and concentrated. The residue was purified by flash column chromatography on silica gel (PE/EA = 20: 1) to afford compound 4 of example A (0.75 g, 28% yield) as a white solid. | |
With sodium carbonate; In tetrahydrofuran; water; at 20℃; for 18h;pH 8 - 9; | General procedure: To 250 mL round-bottomed flask add 1a or 1c or 1g or 1h, 2.5 equiv Fmoc-OSu, 50 mL THF/H2O (1:1, v/v), pH of the solution was adjusted with saturated sodium carbonate to 8-9, and the reaction continued at room temperature for about 18h. After that, the solution was extracted twice with ether, and pH of aqueous layer was adjusted with concentrated HCl to 5, white precipitation was obtain and dried in vacuum to gave corresponding product (2a or 2c or 2g or 2h). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
0.36 g (0.35 mmole, 44%) | In methanol; acetonitrile; | EXAMPLE 10 Rapamycin 42-ester with 1-aminocyclopentane carboxylic acid To a chilled (ice bath) solution of rapamycin 42-ester with 1-(9H-fluoren-9-ylmethoxycarbonylamino)-cyclopentane carboxylic acid (0.991 g, 0.794 mmol) in acetonitrile (4.5 mL) was added 0.47 mL (4.76 mmol) of piperidine in 2 mL of acetonitrile via an additional funnel. The reaction mixture was stirred at 0-5 C. for about two hours (a white precipitate formed after an hour). The reaction mixture was then filtered and concentrated (without heating) and applied to a flash column with a gradient of 1-1.5% methanol/chloroform to yield 0.36 g (0.35 mmole, 44%) of the title compound. Negative FAB-MS [M-H]- am/z 1024. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
16.6% | In 1,4-dioxane; alumina-filtered dioxane; | EXAMPLE 8 1-(9H-Fluoren-9-ylmethoxycarbonylamino)-cyclopentane carboxylic acid To a chilled (ice bath) suspension of aminocyclopentanecarboxylic acid (1.05 g, 8.13 mmol) in alumina-filtered dioxane (8 mL) was added 10% Na2 CO3 (16.5 mL). The reaction mixture became clearer (but not completely clear) after 10% Na2 CO3 was added. A solution of a fluorenylmethyl chloroformate (2.11 g, 8.16 mmol in 12 mL dioxane) was then slowly added to the reaction mixture, which became (and remained) cloudy. The reaction mixture was allowed to warm to room temperature (~20 C.) and was stirred overnight under N2. The reaction mixture was poured into ice water (~150 mL) and extracted three times with anhydrous ether. (Some product went into the ether layer). The aqueous layer was chilled in an ice bath, acidified with concentrated HCl to pH of about 2, and extracted three times with ethyl acetate (3*50 mL). The combined ethyl acetate layers were washed with 0.1N HCl and H2 O. The ether and ethyl acetate layers were dried over MgSO4, combined and concentrated. Flash chromatography (40-50% ethyl acetate/hexane) gave the title compound as a white foam in a yield of 16.6% (0.476 g (1.35 mmol). DEI m+am/z 351. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
56% | (S)-(9H-Fluoren-9-yl)methyl l-(l-cyano-2-(4'-((4-methylpiperazin-l-yl)methyl) biphenyl-4-yl)ethylcarbamoyl)cyclopentylcarbamate (Fmoc-PZ1044)DMTMM (663 mg, 2.4 mmol) was added to a solution of compound PZ1024-6 from example 1 (400 mg, 1.2 mmol) in DCM (25.0 mL) in an ice-water bath. The mixture was stirred at 0C for 0.5 h and compound 4 from example A described in the MATERIALS AND METHODS section (444 mg, 1.32 mol) was added. The reaction mixture was allowed to warm to room temperature and stirred for 12 h. Water was added and the resulting mixture was extracted with DCM. The combined extracts were washed with brine, dried over anhydrous Na2S04 and concentrated. The residue was purified by flash column chromatography on silica gel (PE/EA = 1 : 1 then EA/MeOH = 40 : 1) to afford compound Fmoc-PZ1044 (452 mg, 56% yield) as a white solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With benzotriazol-1-ol; N-ethyl-N,N-diisopropylamine; diisopropyl-carbodiimide; In tetrahydrofuran; at 20℃; for 18h; | General procedure: To a 100 mL round-bottomed flask add equimolar 2a and 2b, 1.2 equiv 1-hydroxybenzotriazole (HOBt), 1.2 equiv DIC, 2.5 equiv N,N-diisopropylethylamine (DIEA), the mixture was stirred in about 30mL dry THF at room temperature for 18h. The solvents were removed in vacuo to give white solid 3a, without further purification, 3a was subjected to 16mL DMF and 4mL piperidine for 30min. The product was added 100 mL deionized water, and extracted twince with 20mL CH2Cl2, dried over anhydrous sodium sulfate. The solvents were removed in vacuo, flash chromatography of the residue on silica gel (CH2Cl2/CH3OH=8:1, v/v) gave pure product 4a. Compounds 4b-4g were prepared with the same procedure. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With N-ethyl-N,N-diisopropylamine; HATU; In dichloromethane; for 18h; | To 6 (287 mg, 0.801 mmol, 1 eq.) in dichloromethane (4 mL, 0.2 M) were added l- [(9H-fluoren-9-ylmethoxy)carbonyl]amino}cyclopentanecarboxylic acid (309 mg, 0.879 mmol, 1.1 eq.), diisopropylethylamine (281 mu, 1.60 mmol, 2 eq.) and HATU (376 mg, 0.960 mmol, 1.2 eq.). The mixture was stirred for 18 hours and diluted with ethyl acetate (15 mL). The reaction mixture was washed with 1 M aqueous hydrochloric acid solution (2 x 5 mL) and with brine (5 mL). The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The crude material was purified by silica gel chromatography (Gradient: 0% to 60% ethyl acetate in heptane) to provide 27 (502 mg, 91%) as a white foam. LC-MS: m/z 692.3 [M+H+], 714.3 [M+Na+], 636.3 [(M - 2-methylprop- l-ene)+H+], retention time = 1.13 minutes; *H NMR (400 MHz, DMSO-i), characteristic signals: delta 7.89 (br d, J=7.4 Hz, 2H), 7.67-7.75 (m, 2H), 7.60 (br s, 1H), 7.38-7.44 (m, 2H), 7.30-7.36 (m, 2H), 7.21 (br d, J=8.8 Hz, 1H), 4.44-4.59 (m, 2H), 4.17-4.27 (m, 3H), 3.68-3.78 (br m, 1H), 3.21 (s, 3H), 2.88 (br s, 3H), 2.09-2.20 (m, 2H), 1.39 (s, 9H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
General procedure: To the resin 13 (560 mg) in DMF (2.5 mL) were added a solutionof the appropriate Fmoc-protected amino acid (see Tables 1-3)(0.3 M), PyBOP (0.3 M) and HOBt (0.3 M) in dry DMF (4.2 mL). Thesuspensions were stirred for 3 min and then DIPEA (0.6 M) wasadded. The suspensions were stirred for 3 h under an argon atmosphereat rt. The resins were washed successively with DCM(150 mL), MeOH (120 mL), DCM (75 mL) and dried overnight undervacuum to give resins 14, each bearing an appropriate Fmoc-protectedamino acid. To the resins 14 (161 mg, 0.13 mmol) wereadded a solution of piperidine (20%, v/v) in DCM (2.1 mL) and themixtures were stirred for 1 h at rt. After filtration, the resins werewashed successively with DCM (50 mL), MeOH (45 mL), DCM(25 mL) and dried under vacuum to give resins 15. Portions(65 mg) of resins 15 were placed in reactor wells (12 mL) of anautomated synthesizer reaction block (40-well format) (AdvancedChemTech). To each well was added a solution of appropriate carboxylicacid (see Tables 1-3) (0.3 M), PyBOP (0.3 M) and HOBt 6-Cl(0.3 M) and DIPEA (0.6 M) in dry DMF (2 mL). The suspensionswere vortexed at 300 rpm over a period of 5 h under an argonatmosphere. The wells were then filtered to remove the reactivesolution from the resins 16 and washed successively with THF,DCM, MeOH and DCM. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
6.4 mg | General procedure: Example 1001 was prepared on Rink Resin following the general synthetic procedures: Fmoc-Gly-OH "Symphony Method B: Resin-swelling procedure" was followed Fmoc-Cys(Trt)-OH "Symphony Method B: Standard-coupling procedure " was followed Fmoc-Arg(Pbf)-OH "Symphony Method B: Standard-coupling procedure " was followed Fmoc-nMethyl-Nle-OH "Symphony Method B: Standard-coupling procedure " was followed Fmoc-nMethyl-Nle-OH "Symphony Method B: Secondary amine-coupling procedure", was followed Fmoc-Trp(Boc)-OH "Symphony Method B: Secondary amine-coupling procedure", was followed Fmoc-Ser(tBu)-OH "Symphony Method B: Standard-coupling procedure " was followed Fmoc-Trp(Boc)-OH "Symphony Method B: Standard-coupling procedure " was followed Fmoc-Cyclopenty-Gly-OH "Manual Coupling procedure A" was followed Fmoc-Leu-OH "Symphony Method B: Secondary amine-coupling procedure", was followed Fmoc-His(Trt)-OH "Symphony Method B: Standard-coupling procedure " was followed Fmoc-Pro-OH "Symphony Method B: Standard-coupling procedure " was followed Fmoc-Asn(Trt)-OH "Symphony Method B: Secondary amine-coupling procedure", was followed Fmoc-nMethyl-Ala-OH "Symphony Method B: Standard-coupling procedure " was followed Fmoc-Phe-OH "Symphony Method B: Secondary amine-coupling procedure" was followed "Symphony Method B: Final capping procedure" was followed "Global Deprotection Method F" was followed "Cyclization Method D" was followed The crude material was purified via preparative LC/MS with the following conditions: Column: Waters XBridge C18, 19 x 250 mm, 5-mupiiota particles; Mobile Phase A: 5:95 acetonitrile: water with 0.1% trifluoroacetic acid; Mobile Phase B: 95:5 acetonitrile: water with 0.1% trifluoroacetic acid; Gradient: 15- 65% B over 25 minutes, then a 5-minute hold at 100% B; Flow: 20 mL/min. Fractions containing the desired product were combined and dried via centrifugal evaporation. The yield of the product was 6.4 mg, and its estimated purity by LCMS analysis was 100%. Analysis LCMS Condition D : Retention time = 1.67 mm; ESI-MS(+) m/z 947.2 (M+2H). Analysis LCMS Condition E. : Retention time = 1.57 min; ESI-MS(+) m/z 946.7 (M+2H). |
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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 |
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