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Synonyms: N-(Fmoc-oxy)succinimide; FMOC-Succinimide; N-(9-Fluorenylmethoxycarbonyloxy)succinimide
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Batch number can be found on the product's label following the word 'Batch'.
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CAS No. : | 82911-69-1 |
Formula : | C19H15NO5 |
M.W : | 337.33 |
SMILES Code : | O=C(N1OC(OCC2C3=C(C4=C2C=CC=C4)C=CC=C3)=O)CCC1=O |
Synonyms : |
N-(Fmoc-oxy)succinimide; FMOC-Succinimide; N-(9-Fluorenylmethoxycarbonyloxy)succinimide
|
MDL No. : | MFCD00010733 |
InChI Key : | WMSUFWLPZLCIHP-UHFFFAOYSA-N |
Pubchem ID : | 134122 |
GHS Pictogram: |
![]() ![]() ![]() |
Signal Word: | Danger |
Hazard Statements: | H315-H318-H335-H411 |
Precautionary Statements: | P261-P264-P271-P280-P302+P352-P304+P340-P305+P351+P338-P310-P362+P364-P403+P233-P501 |
Class: | 9 |
UN#: | 3077 |
Packing Group: | Ⅲ |
* 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 |
---|---|---|
98% | With sodium hydrogencarbonate In water; acetone for 3 h; | This compound was synthesized according to the synthetic scheme described in FIGURE 6. To the solution 6-chloroindole (500 mg, 3.31 mmol, I eq) in acetic acid (10 mL) L-serine (695 mg, 6.62 mmol, 2 eq) and acetic anhydride (3.1 mL, 33.1 mmol, 10 eq) were added and the mixture was stirred under Ar at 73°C for 4 h. The reaction mixture was concentrated to half of the volume, diluted with water and extracted with EtOAc. The organic layers were combined, dried over sodium sulfate and evaporated to yield crude product N°-acetyl-6-chloro-D,L-tryptophan 686 mg, 74percent yield). 111 NMR (500 MHz, CD3OD) 81.91 (s, 3H), 3.15-3.3 1 (m, 2H), 4.67 (t, IH), 6.97 (dd, IH), 7.10 (s, 1H), 7.33 (d, IH), 7.53 (d, IH). The A°-acetyl-6-chloro-D,L-tryptophan (686 mg, 145 mmol) was dissolved in phosphate buffer (50 mL) containing 1 mM CoCl26H2O and pH 8.0. To the reaction mixture acylase I was added (500 mg) and the reaction was stirred at 37°C for 24 h with occasional adjustment of pH to 8.0 with LIOH. The reaction mixture was heated to 60°C for 5 mm, cooled to room temperature and filtered through celite. The filtrate was acidified to pH around 3 using HCI and extracted with EtOAc. The aqueous layer was lyophilized and used as crude product for the next reaction. Estimated yield of 43percent (based on theoretical yield for the Lenantiomer), 125.4 mg. 6-chloro-L-tryptophan (125.4 mg, 0.527 mmol, 1 eq) was dissolved in a water/acetone mixture (1:1, v/v) to which NaHCO3 (88.5 rng, 1.05 mmol, 2 eq) was added. Fmoc-OSu (195.6 rng, 0.58 mmol, 1.1 eq) was dissolved in acetone and added to the reaction mixture portion wise over the course of 3 h. Following reaction completion the acetone was evaporated and the aqueous layer acidified with acetic acid to pH about 3 followed by EtOAc extraction. The organic layers were combined, dried over sodium sulfate and evaporated. The crude product was purified with flash column chromatography and solvent system hexanes:EtOAc:AcOH (10:9:1) to yield pure Fmoc-6-chloro-L-tryptophan (237 mg, 98percent). ‘H NMR (500 MHz, CD3OD), 83.16-3.32 (m, 211), 4.65 (t, 1H), 6.98 (dd, 1H), 7.12 (s, 1H), 7.3- 7.55 (m, 8H), 7.79 (d, 211). MS (ESI) calculated for C26H21C1N204 [M+Hj: m/z 460.12, found460.4. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; In methanol; N,N-dimethyl-formamide; at 20℃; for 3h; | A suspension of Amphotericin B (15.0g. 16.23 mmol)) in 2:1 DMF:MeOH(707 ml) was treated with pyridine (8.0 nit, 93.33 mrnol.) and Frnoc-Succ (8.2 g, 24.35 mrnoi) at room temperature. After 3 h the reaction mixture was poured into Et20 at 0C and stirred for 30 mm to precipitate out the product. The crude product was collected and washed with additional and dried in vaeuo. The crude product was dissolved in THF:MeOH (1:1, 360 rnL) at 0 C. The solution was then treated with CSA (1.6 g, 6.81 mmol). After I h, the reaction was quenched at 0 C with triethyianiine (870 iL, 6.81 mmol) and filtered. The filtrate was concentrated to half the starting volume poured into a solution of hexanes:Et20 (1:1. 5L). The resulting crashed out solid was collected to provide compound 54 (8.Og, 43%) as a yellow solid. LC/MS (ESI) rn/i 1058.5 [MJ-IF. | |
A round bottom flask was charged with amphotericin B (0.5 g, ca. 1.082 mmol, 1 eq) and Fmocsuccinimide (0.28 g, 0.81 mmol, 1.5 eq) which were dissolved in a 2: 1 mixture ofDMF:MeOH (16.9 mL) at room temperature. Pyridine (0.25 mL, 3.10 mmol, 5.74 eq) was subsequently added and the reaction was stirred for 12 hours at room temperature. The reaction mixture was then poured into diethyl ether (0.5 L). After stirring for 30 minutes, the resulting yellow precipitate was isolated via Biichner filtration using Whatman 50 filter paper to afford a yellow solid. The filter cake was dried on the filter for 10 minutes and then stored under vacuum for one hour.The resulting powder was dissolved in 1 : 1 THF:MeOH (18 mL) and cooled to 0C. To this solution was added camphorsulfonic acid (69 mg, 0.30 mmol, 0.55 eq) and the resulting mixture was stirred for 1 hour at 0C. The reaction was then quenched at 0C with triethylamine (0.07 mL, 0.30 mmol, 0.55 eq). The reaction was concentrated in vacuo removing approximately half of the solvent. The resulting saturated solution was poured into 1 : 1 hexanes: diethyl ether (0.5 L) and the yellow precipitate was collected via Biichner filtration using Whatman 50 filter paper and washed with diethyl ether (100 mL) to yield a yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | With sodium hydrogencarbonate; sodium carbonate; In water; acetone; | General procedure: Suitable N-protected amino alcohols (e.g. Fmoc and boc) can be obtained by reacting an amino alcohol with a desired protecting group precursor that protects the amine group with the desired protecting group Pgi . For example, N-Fmoc protected amino alcohols were prepared (in an Erlenmeyer flask) by suspending/dissolving Fmoc-O-Su in acetone (in a ratio of about 2.5-6 mL acetone per mmol of Fmoc-O-Su) with stirring. To this briskly stirring solution was added dropwise a solution of the amino alcohol (in a ratio of about 1 to 1 .2 eq. per mmol of Fmoc-O-Su) dissolved in acetone (in a ratio of about 0.4- 1 .2 mL acetone per mmol of the amino alcohol) and occasionally some water if the amino alcohol is not completely soluble in the acetone alone. When addition was complete, a solution containing NaHC03 and Na2C03 (in a ratio of about 1 to 1 .1 mmol NaHC03 and 0.5 to 0.55 mmol Na2C03 per mmol of Fmoc-O-Su) dissolved in deionized water (in a ratio of about 1 mL deionized water per 1 mL of acetone originally added to the Fmoc-O-Su) was added dropwise to the stirring reaction. After stirring and analysis by TLC (indicating complete reaction), a solution containing enough HCI (dissolved in about 0.3 mL water per 1 mL of acetone originally added to the Fmoc-O-Su) to completely neutralize the NaHC03 and Na2C03 was added dropwise over 30 minutes to one hour. The pH of the solution was then adjusted to approximately 4-5 (pH paper) by addition of 1 N HCI. The flask was then heated on a hot plate stirrer until the solid dissolved. The solution was then allowed to cool overnight and the product crystallized. The crystalline product was then collected by vacuum filtration. The product was then optionally recrystallized (usually by a mixture of acetonitrile and water) to the desired level of purity. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine; In methanol; | H-GF-OH will be dissolved in methanol followed by the addition of pyridine. FmocOSu will be added to the reaction mixture and stirred overnight. The reaction mixture will be concentrated under vacuum followed by trituration with diethyl ether. This will be purified by column chromatography (silica gel) using ethyl acetate (EtOAc) and methanol as eluent. The fractions containing Fmoc-GF-OH will be concentrated and used in subsequent reaction without thrther purification. H-EG-OH will be dissolved in methanol and cooled to 0 C. followed by the addition of 50C12. The reaction mixture will be refluxed followed by the removal of solvent under vacuum. The product will be redissolved in toluene and concentrated under vacuum to remove traces of methanol and 50C12. The solid (EGOMe) will be dissolved in EtOAc and Fmoc-GF-OH will be added to it followed by the addition of DIPEA and HOP and stirred overnight. The solvent will be removed under vacuum and washed with H20 and extracted with EtOAc. The product will be purified by column chromatography (silica gel, eluent EtOAc:methanol; 9:1 v/v). The fraction containing Fmoc-GFEG-OMe will be concentrated under vacuum. Fmoc-GFEG-OMe will be dissolved in methanol and aqueous iN NaOH will be added dropwise at room temperature and stirred for 6 hours. The reaction mixture will be concentrated to 50% the volume and the pH of the solution will be adjusted to pH 3. The precipitate will be extracted with EtOAc. The EtOAc layer will be concentrated to give FmocGFEG-OH. The product will be identified by mass spectrometry. Fmoc-GFEG-OH will be dissolved in DMF (anhydrous) and cooled in an ice bath to -15 C., an excess of DCC solution will be added dropwise with constant stirring followed by an excess of p-nitrophenol (ONp) solution. The reaction mixture will be stirred for 3 hat-i 5C., followed by overnight at 4 C. and an additional 24 hat room temperature. Trace amounts of acetic acid (glacial) will be added to the solution to react with excess DCC. The precipitated byproduct DCU will be removed and the filtrate concentrated to obtain the product (Fmoc-GFEG-ONp). Recrystallization will be done from EtOH/H20 1:1 (v/v). Fmoc-GFEG-ONp will be dissolved in DCM followed by the addition of bocethylenediamine and TEA. The reaction mixture will be stirred and then concentrated followed by purification by colunm chromatography (silica gel, eluent EtOAc). The fractions containing Fmoc-GFEG-ED-Hoc was concentrated and analyzed by mass spectroscopy. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
13% | 8-(((9H-Fluoren-9-yl)methoxy)carbonylamino)-l,4-dioxaspiro[4.5]decane-8- carboxylic acid (compound 3 of example A): After the solution of compound 2 of example A was adjusted to pH = 10 with 2 N HCI, Fmoc-Osu (15.87 g, 45.0 mmol) and acetonitrile (50.0 mL) were added. 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 (DCM/MeOH = 50: 1) to affordcompound 3 of example A (5.0 g, 13% yield over three steps) as a white solid. | |
213 mmol (42.9 g) of <strong>[54621-18-0]8-amino-1,4-dioxaspiro[4,5]decane-8-carboxylic acid</strong> in 213 ml of 1N NaOH and 213 mmol (71.9 g) of Fmoc-ONSu in 240 ml of acetonitrile are combined and diluted with 1000 ml of acetonitrile/H2O 1:1. After the pH is set at 9, it is stirred overnight at room temperature. After the acetontrile is removed in a rotary evaporator, it is acidified with 0.01 M HCl and extracted with ethyl acetate. The extract is washed neutral, dried with Na2SO4 and evaporated to the dry state. The residue is recrystallized from ethyl acetate/hexane. Yield: 79.0 g of 8-[[(9H-fluoren-9-ylmethoxy)carbonyl]amino]-1,4-dioxaspiro[4,5]decane-8-carboxylic acid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Aminomethylcyclohexane carboxylic acid (1) (20 g, 127 mmol) and sodium carbonate (13.6 g, 128 mmol) were dissolved in 600 mL of water, then a solution of FmocOSu (40 g, 118 mmol) was added over a period of 30 min with stirring. The mixture was stirred overnight, during which a large amount of white precipitate formed. The mixture was acidified to pH=3 with 1N HCl, then diluted with 2L of ethyl acetate. The organic layer was separated, washed with 5percent aqueous citric acid, water and brine. The organic layer was dried over anhydrous sodium sulfate, filtered and cooled in a freezer overnight. The solid was filtered off, then the filtrate was concentrated to ca. 1L and cooled overnight. The solid was filtered and combined with the previously collected solid (2) then dried in a desiccator. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In diethyl ether; acetonitrile; | (a) Synthesis of N1 -Fluoren-9-ylmethoxycarbonyl-N2 -succinimido-oxy-carbonylhydrazine (Fmoc-Azgly-OSu) A solution of 95percent aqueous hydrazine (1.28 ml) in acetonitrile (100 ml) was added dropwise during 2 hours at laboratory temperature to a stirred solution of fluoren-9-ylmethyl succinimido carbonate (Fmoc-OSu, 13.48 g) in acetonitrile (200 ml) and the mixture was stirred for a further 16 hours and then filtered. The solid residue was washed with a 1:1 v/v mixture of acetonitrile and diethyl ether and then with diethyl ether, and then dried. There was thus obtained fluoren-9-ylmethoxycarbonylhydrazine (Fmoc-hydrazine, 7.81 g). A further 0.96 g of this material was obtained by concentration of the filtrate and washings, filtration and crystallisation of the solid residue from ethanol. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
<Synthesis of Ia, Ig and Ic>7.68 g (50 mmol) of N-methylamino butyric acid hydrochloride was dissolved in 50 mL of water, 4.20 g (50 mmol) of NaHCO3 was added, and all of these were agitated for 10 min. This solution was agitated for two days at room temperature, with 13.49 g (40 mmol) of 9-fluorenylmethyl succinimidyl carbonate, 100 mL of acetonitrile and 0.14 g (0.4 mmol) of tetrabutylammonium hydrogen sulfide added. After being concentrated under reduced pressure, the solution was diluted with methylene chloride and washed with water. After being concentrated under reduced pressure and subjected twice to azeotropy with dehydrated acetonitrile, the methylene chloride solution was subjected to azeotropy with dehydrated methylene chloride. A residue was dissolved in 200 mL of dehydrated methylene chloride, 4.13 g (20 mmol) of N,N'-dicyclohexylcarbodiimide was added at 0° C., and all of these were agitated for 2 hr at room temperature. After unnecessary materials were filtered out, this solution was concentrated under reduced pressure, and a residue A was obtained.A deoxynucleoside (dA, dG or dC, 20 mmol) was suspended in dehydrated pyridine, and these were concentrated under reduced pressure three times. A residue was suspended in 100 mL of dehydrated pyridine, 8.45 mL (66 mmol) of trimethylchlorosilane was added at 0° C., all of these were agitated for 1 hr at room temperature and then cooled to 0° C. again, and this solution was introduced into the residue A. A reaction mixture was agitated for 2 hr at room temperature. With 20 mL of water added under ice-cold conditions, the reaction mixture was then agitated overnight at room temperature. This solution was diluted with methylene chloride and washed with water. The methylene chloride solution was concentrated under reduced pressure, and a residue was purified by medium-pressure chromatography (dichloromethane-ethanol 19:1 --> 4:1) to yield desired products: 6.91 g (60percent) of Ia, 9.43 g (80percent) of Ig and 8.80 g (80percent) of Ic. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Synthesis of Fmoc-DOPA(acetonide)-OH (7)The oil residue of H-DOPA(acetonide)-OMe (0.50 g, 2 mmol) was dissolved in 20 mL THF and cooled in an ice bath. Lithium hydroxide (0.96 g, 4 mmol) in cold water (7 mL) was added. The mixture was stirred at 0 C. for 2.5 h, treated with 1N HCl to a pH of 7-8, followed by addition of Na2CO3 (0.42 g, 4 mmol). Fmoc-OSu (0.68 g, 2 mmol) was added and the mixture was stirred at 0 C. for another 2 h. The mixture was then acidified with 1N HCl to a pH of 2-3. After THF was reduced by rotary evaporation, the mixture was extracted with EtOAc. The organic phase was washed with water, dried over MgSO4, concentrated to minimum amount. To the residue was added hexane, and the white precipitate was collected and purified by silica-gel flash chromatography (washed with DCM, and then eluted with DCM/EtOAc/MeOH (67:30:3), yield, 0.66 g (74%).Spectral Data. 1H NMR (500 MHz, CDCl3): delta 11.15 (br, 1H), 7.81-7.28 (m, 8H), 6.71-6.54 (m, 3H), 5.41 (d, 1H), 4.72 (m, 1H), 4.52-4.24 (m, 3H), 3.18-3.06 (m, 2H), 1.67 (s, 6H). 13C NMR (125 MHz, CDCl3): delta 176.5, 156.1, 147.8, 146.8, 143.92, 143.81, 141.4 (2C), 128.6, 127.9 (2C), 127.3 (2C), 125.28, 125.22, 122.1, 119.9 (2C), 118.2, 109.6, 108.4, 67.3, 54.9, 47.2, 37.6, 26.0 (2C). 13C NMR (125 MHz, CDCl3) DEPT: CH3, 26.0; CH2, 67.3, 37.6; CH, 127.9, 127.3, 125.28, 125.22, 122.1, 119.9, 109.6, 108.4, 54.9, 47.2. Ferric Chloride Test: negative at room temperature, positive at 105 C. ESI-MS: MH+, Calcd. 460.18. Found 459.85; M2Na+, Calcd. 941.33, Found 940.77. M3Na+, Calcd. 1400.49, Found 1400.49; M4Na+, Calcd. 1860.67, Found 1859.36. HRMS (ESI): C27H25NO6, MH+, Calcd. 460.17546, Found 460.17516 (FIG. 31). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | 7.68 g (50 mmol) of N-methylaminobutyrate hydrochloride was dissolved in 50 mL of water and 4.20 g (50 mmol) of NaHCO3 was added thereto and agitated for 10 minutes. Then, 13.49 g (40 mmol) of 9-fluorenylmethyl succinimidyl carbonate, 100 mL of acetonitrile and 0.14 g (0.4 mmol) tetrabutylammonium hydrogen sulfate were added to the solution and agitated at room temperature for 2 days. After concentrating the solution under reduced pressure, it was diluted by methylene chloride and washed with water. The methylene chloride solution was then concentrated under reduced pressure and subjected to azeotropy by means of dehydrated acetonitrile and then by means of dehydrated methylene chloride. The residue was dissolved in 200 mL of dehydrated methylene chloride and 4.13 g (20 mmol) of N,N?-dicyclohexylcarbodiimide was added and agitated at room temperature for 2 hours. After filtering the undissolved substance, the solution was concentrated under reduced pressure to obtain residue A. Dioxynucleoside (dA, dG or dC, 20 mmol) was suspended in dehydrated pyridine and an operation of concentrating it under reduced pressure was repeated three times. The residue was suspended in 100 mL of dehydrated pyridine and 8.45 mL (66 mmol) of trimethylchlorosilane was added thereto at 0° C. Then, the mixture solution was agitated at room temperature for 1 hour and subsequently cooled to 0° C. again before it was introduced to the residue A. The reaction mixture was agitated at room temperature for 2 hours. Then, 20 mL of water was added to the reaction mixture while the latter was being cooled with ice and the solution was agitated at room temperature overnight. The solution was diluted by methylene chloride and washed with water. The methylene chloride solution was concentrated under reduce pressure and the residue was purified by medium pressure chromatography (dichloromethane-ethanol 19:1?4:1) to obtain target products Ia, Ig and Ic in amounts of 6.91 g (60percent), 9.43 g (80percent) and 8.80 g (80percent), respectively. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
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 |
---|---|---|
94% | With water; sodium hydrogencarbonate; In tetrahydrofuran; for 2h; | <strong>[159877-12-0](R)-5-amino-2-((tert-butoxycarbonyl)amino)pentanoic acid</strong> (4.77 g, 20.54 mmol) was dissolved in THF (82 ml) followed by the addition of Water (82 ml). SODIUM BICARBONATE (3.45 g, 41.1 mmol) was then added followed by the addition of (9H- fluoren-9-yl)methyl (2,5-dioxopyrrolidin-l-yl) carbonate (6.93 g, 20.54 mmol). The reaction was stirred for 2 h. Most of the THF was removed under vacuum then Et20 was added. The organic layer was discarded and the aqueous layer was again washed with Et20. The aqueous phase was collected, acidified with 1 N HC1, and extraced with EtOAc. The organic layer was collected, dried over sodium sulfate, and concentrated under vacuum to give (R)-5-((((9H-fluoren-9-yl)methoxy)carbonyl)amino)-2-((tert- butoxycarbonyl)amino)pentanoic acid, 8.76 g (94%). ESI-MS(+) m/z 454.9 (M+l). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With sodium hydrogencarbonate; In water; acetonitrile; for 2.0h; | Synthesis of Fmoc-Thr(Me) <strong>[4144-02-9]O-Methyl threonine</strong> (2.663 g, 20 mmol) was dissolved in a solution of sodium bicarbonate (5.04 g, 60 mmol) in water (100 ml). Acetonitrile (50 ml) was added, followed by a suspension of Fmoc-OSu (6.747 g, 20 mmol) in acetonitrile (50 ml), delivered in several portions. The reaction mixture was stirred for 2 hours and, during which time, became homogenous. It was then acidified with 2 M HCl and was diluted with 100 ml of water. The resulting precipitate was collected by filtration, washed with water and dried under vacuum to give the target product as a white powder. Yield: 6.745 g (95%). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
50.3% | A solution of NaOH (600 mg, 15 mmol) in 1 :1 mixture of water/EtOH (10 ml) was bubbled with nitrogen and heated at 40 °C. It was added with L-homocysteine (675.5 mg, 5 mmol), followed by propyl p-toluenesulfonate (1 .09 g, 5.05 mmol). The mixture was stirred under nitrogen at 40 °C for 1 .5 hours, then to room temperature overnight. EtOH was partially removed by rotary evaporation, and the residue was extracted with DCM (~ 30 ml). THF (10 ml) was added to the aqueous solution, followed by Fmoc- Osu (1 .7 g, 5 mmol). After the mixture was stirred for 1 hour, it was added with an additional amount of Fmoc-Osu (337 mg, 1 mmol). The reaction was continued for one more hour. THF was partially removed by rotary evaporation. The white suspension residue was directly purified through RPLC (150 g, 5 to 58 percent acetonitrile and water, using 0.1 percent TFA as modifier). Yield 1 .05 g, 50.3 percent. Ion found by LCMS: [M+1 ]+ = 400. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With N-ethyl-N,N-diisopropylamine; In water; acetonitrile; at 20℃; for 3h; | General procedure: DIPEA (2-3 eq.) and Fmoc-OSu (0.9 eq) are added to the amino acid or its hydrochloride (1 eq.) in a 1:1 mixture of acetonitrile/water (20 mL/1 mmol amino acid) and the mixture is stirred for at least 90 min at room temperature. After acidification with 1M HCl, the reaction mixture is extracted withdichloromethane (3x). The combined organic phases are washed with brine, dried with MgSO4, filteredand the solvent is evaporated under reduced pressure to afford the crude Fmoc-protected amino acid. If necessary, the residue is crystallized from dichloromethane/hexane to afford the desired product as a solid. |
Tags: Fmoc-OSu | Protective Groups | Organic Building Blocks | 82911-69-1
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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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