Structure of Bis(4-nitrophenyl) carbonate
CAS No.: 5070-13-3
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CAS No. : | 5070-13-3 |
Formula : | C13H8N2O7 |
M.W : | 304.21 |
SMILES Code : | [O-][N+](=O)C1=CC=C(OC(=O)OC2=CC=C(C=C2)[N+]([O-])=O)C=C1 |
MDL No. : | MFCD00007322 |
InChI Key : | ACBQROXDOHKANW-UHFFFAOYSA-N |
Pubchem ID : | 78756 |
GHS Pictogram: |
![]() |
Signal Word: | Warning |
Hazard Statements: | H315-H319 |
Precautionary Statements: | P305+P351+P338 |
Num. heavy atoms | 22 |
Num. arom. heavy atoms | 12 |
Fraction Csp3 | 0.0 |
Num. rotatable bonds | 6 |
Num. H-bond acceptors | 7.0 |
Num. H-bond donors | 0.0 |
Molar Refractivity | 77.18 |
TPSA ? Topological Polar Surface Area: Calculated from |
127.17 Ų |
Log Po/w (iLOGP)? iLOGP: in-house physics-based method implemented from |
1.42 |
Log Po/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by |
3.29 |
Log Po/w (WLOGP)? WLOGP: Atomistic method implemented from |
3.08 |
Log Po/w (MLOGP)? MLOGP: Topological method implemented from |
1.85 |
Log Po/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by |
-1.87 |
Consensus Log Po/w? Consensus Log Po/w: Average of all five predictions |
1.55 |
Log S (ESOL):? ESOL: Topological method implemented from |
-3.81 |
Solubility | 0.0475 mg/ml ; 0.000156 mol/l |
Class? Solubility class: Log S scale |
Soluble |
Log S (Ali)? Ali: Topological method implemented from |
-5.64 |
Solubility | 0.000704 mg/ml ; 0.00000231 mol/l |
Class? Solubility class: Log S scale |
Moderately soluble |
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by |
-3.09 |
Solubility | 0.246 mg/ml ; 0.000809 mol/l |
Class? Solubility class: Log S scale |
Soluble |
GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg |
High |
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg |
No |
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) |
No |
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) |
Yes |
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) |
Yes |
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) |
Yes |
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) |
No |
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) |
Yes |
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from |
-5.82 cm/s |
Lipinski? Lipinski (Pfizer) filter: implemented from |
0.0 |
Ghose? Ghose filter: implemented from |
None |
Veber? Veber (GSK) filter: implemented from |
0.0 |
Egan? Egan (Pharmacia) filter: implemented from |
0.0 |
Muegge? Muegge (Bayer) filter: implemented from |
0.0 |
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat |
0.55 |
PAINS? Pan Assay Interference Structures: implemented from |
0.0 alert |
Brenk? Structural Alert: implemented from |
3.0 alert: heavy_metal |
Leadlikeness? Leadlikeness: implemented from |
No; 1 violation:MW<0.0 |
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) |
2.3 |
* 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 |
---|---|---|
With triethylamine; In dichloromethane; at 0 - 20℃; for 2.5 - 4h;Product distribution / selectivity; | Example 4; Synthesis of the compound (L-R); Reaction scheme:Process:1 g 3-(l-(Dimethylamino)ethyl) phenol was dissolved in 20 ml dichloromethane (distilled from CaCl2). The solution was cooled with an ice-water bath (0-50C). 0.92 g trie thy lamine was added.2.21 g bis(4-nitrophenyl)carbonate was added. The yellow solution was stirred in an ice- water bath.[0062] Reaction progress was monitored by HPLC. After 4 hours, 715 mg N- ethylmethylamine was added and the yellow solution was stirred for 17 hours at 40C. The reaction mixture was allowed to warm to room temperature and was then washed with 2x20 ml water. The organic phase was concentrated in vacuo. To the resulting yellow oil, 20 ml diethyl ether and 20 ml of a solution of hydrochloric acid (2 M) were added. The 2- phase system was stirred for 15 minutes. The acidic aqueous layer was washed with 20 ml diethyl ether.[0063] 20 ml dichloromethane was added to the aqueous layer and a solution of sodium hydroxide (2 M) was added until pH~12 was reached. The organic layer was washed with 2x20 ml water, dried (Na2SO4), filtered and concentrated in vacuo. <n="19"/>Isolated yield: 1.37 g (90%), yellow oilHPLC: 98% purity1H-NMR: confirmed the expected structure; Example 5; Synthesis of the compound (JL-R); [0064] 1 g 3-(l-(Dimethylamino)ethyl) phenol was dissolved in 20 ml dichloromethane (distilled from CaCl2).[0065] 0.92 g triethylamine was added.[0066] 2.21 g bis(4-nitrophenyl)carbonate was added. The yellow solution was stirred at ambient temperature. [0067] Reaction progress was monitored by HPLC. After 2.5 hours, 715 mg JV- ethylmethylamine was added dropwise and the yellow solution was stirred for 1.5 hours at ambient temperature. The reaction mixture was washed with 2x20 ml water. The organic phase was concentrated in vacuo. To the resulting yellow oil, 20 ml diethyl ether and 20 ml of a solution of hydrochloric acid (2 M) were added. The 2-phase system was stirred for 15 minutes. The acidic aqueous layer was washed with 20 ml diethyl ether.[0068] 20 ml dichloromethane was added to the aqueous layer and a solution of sodium hydroxide (2 M) was added until pH~12 was reached. The organic layer was washed with 2x20 ml water, dried (Na2SO4), filtered and concentrated in vacuo.Isolated yield: 1.36 g (90%), yellow oil HPLC: 97% purity1H-NMR, 13CNMR: confirmed the expected structure Examples 6-9 | |
With triethylamine; In ethyl acetate; at 0 - 5℃; for 2.5h;Product distribution / selectivity; | Example 5; Synthesis of the compound (JL-R) [0064] 1 g 3-(l-(Dimethylamino)ethyl) phenol was dissolved in 20 ml dichloromethane (distilled from CaCl2).[0065] 0.92 g triethylamine was added.[0066] 2.21 g bis(4-nitrophenyl)carbonate was added. The yellow solution was stirred at ambient temperature. [0067] Reaction progress was monitored by HPLC. After 2.5 hours, 715 mg JV- ethylmethylamine was added dropwise and the yellow solution was stirred for 1.5 hours at ambient temperature. The reaction mixture was washed with 2x20 ml water. The organic phase was concentrated in vacuo. To the resulting yellow oil, 20 ml diethyl ether and 20 ml of a solution of hydrochloric acid (2 M) were added. The 2-phase system was stirred for 15 minutes. The acidic aqueous layer was washed with 20 ml diethyl ether.[0068] 20 ml dichloromethane was added to the aqueous layer and a solution of sodium hydroxide (2 M) was added until pH~12 was reached. The organic layer was washed with 2x20 ml water, dried (Na2SO4), filtered and concentrated in vacuo.Isolated yield: 1.36 g (90%), yellow oil HPLC: 97% purity1H-NMR, 13CNMR: confirmed the expected structure Examples 6-9; The Example 5 was repeated in the following solvents and with the following results: | |
With triethylamine; In acetonitrile; at 0 - 5℃; for 2.5h;Product distribution / selectivity; | Example 5; Synthesis of the compound (JL-R) [0064] 1 g 3-(l-(Dimethylamino)ethyl) phenol was dissolved in 20 ml dichloromethane (distilled from CaCl2).[0065] 0.92 g triethylamine was added.[0066] 2.21 g bis(4-nitrophenyl)carbonate was added. The yellow solution was stirred at ambient temperature. [0067] Reaction progress was monitored by HPLC. After 2.5 hours, 715 mg JV- ethylmethylamine was added dropwise and the yellow solution was stirred for 1.5 hours at ambient temperature. The reaction mixture was washed with 2x20 ml water. The organic phase was concentrated in vacuo. To the resulting yellow oil, 20 ml diethyl ether and 20 ml of a solution of hydrochloric acid (2 M) were added. The 2-phase system was stirred for 15 minutes. The acidic aqueous layer was washed with 20 ml diethyl ether.[0068] 20 ml dichloromethane was added to the aqueous layer and a solution of sodium hydroxide (2 M) was added until pH~12 was reached. The organic layer was washed with 2x20 ml water, dried (Na2SO4), filtered and concentrated in vacuo.Isolated yield: 1.36 g (90%), yellow oil HPLC: 97% purity1H-NMR, 13CNMR: confirmed the expected structure Examples 6-9; The Example 5 was repeated in the following solvents and with the following results: |
With triethylamine; In tetrahydrofuran; at 0 - 5℃; for 2.5h;Product distribution / selectivity; | Example 5; Synthesis of the compound (JL-R) [0064] 1 g 3-(l-(Dimethylamino)ethyl) phenol was dissolved in 20 ml dichloromethane (distilled from CaCl2).[0065] 0.92 g triethylamine was added.[0066] 2.21 g bis(4-nitrophenyl)carbonate was added. The yellow solution was stirred at ambient temperature. [0067] Reaction progress was monitored by HPLC. After 2.5 hours, 715 mg JV- ethylmethylamine was added dropwise and the yellow solution was stirred for 1.5 hours at ambient temperature. The reaction mixture was washed with 2x20 ml water. The organic phase was concentrated in vacuo. To the resulting yellow oil, 20 ml diethyl ether and 20 ml of a solution of hydrochloric acid (2 M) were added. The 2-phase system was stirred for 15 minutes. The acidic aqueous layer was washed with 20 ml diethyl ether.[0068] 20 ml dichloromethane was added to the aqueous layer and a solution of sodium hydroxide (2 M) was added until pH~12 was reached. The organic layer was washed with 2x20 ml water, dried (Na2SO4), filtered and concentrated in vacuo.Isolated yield: 1.36 g (90%), yellow oil HPLC: 97% purity1H-NMR, 13CNMR: confirmed the expected structure Examples 6-9; The Example 5 was repeated in the following solvents and with the following results: | |
With triethylamine; In acetone; at 0 - 5℃; for 2.5h;Product distribution / selectivity; | Example 5; Synthesis of the compound (JL-R) [0064] 1 g 3-(l-(Dimethylamino)ethyl) phenol was dissolved in 20 ml dichloromethane (distilled from CaCl2).[0065] 0.92 g triethylamine was added.[0066] 2.21 g bis(4-nitrophenyl)carbonate was added. The yellow solution was stirred at ambient temperature. [0067] Reaction progress was monitored by HPLC. After 2.5 hours, 715 mg JV- ethylmethylamine was added dropwise and the yellow solution was stirred for 1.5 hours at ambient temperature. The reaction mixture was washed with 2x20 ml water. The organic phase was concentrated in vacuo. To the resulting yellow oil, 20 ml diethyl ether and 20 ml of a solution of hydrochloric acid (2 M) were added. The 2-phase system was stirred for 15 minutes. The acidic aqueous layer was washed with 20 ml diethyl ether.[0068] 20 ml dichloromethane was added to the aqueous layer and a solution of sodium hydroxide (2 M) was added until pH~12 was reached. The organic layer was washed with 2x20 ml water, dried (Na2SO4), filtered and concentrated in vacuo.Isolated yield: 1.36 g (90%), yellow oil HPLC: 97% purity1H-NMR, 13CNMR: confirmed the expected structure Examples 6-9; The Example 5 was repeated in the following solvents and with the following results: | |
In dichloromethane; at 20℃; for 2h;Product distribution / selectivity; | Example 10; Synthesis of the compound (I-R); [0070] 0.5 g 3-(l-(Dimethylamino)ethyl) phenol was dissolved in 10 ml dichloromethane (distilled from CaCl2).[0071] 1.1 g bis(4-nitrophenyl)carbonate was added. The yellow solution was stirred at ambient temperature.[0072] Reaction progress was monitored with HPLC. After 2 hours, 358 mg N- ethylmethylamine was added dropwise and the yellow solution was stirred at ambient temperature for 16 hours. The reaction mixture was concentrated in vacuo. To the resulting yellow oil, 20 ml diethyl ether and 20 ml of a solution of hydrochloric acid (2 M) were added. The 2-phase system was stirred for 15 minutes. The acidic aqueous layer was washed with 20 ml diethyl ether.[0073] 20 ml dichloromethane was added to the aqueous layer and a solution of sodium hydroxide (2 M) was added until pH~12 was reached. The organic layer was washed with 2x20 ml water, dried (Na2SO4), filtered and concentrated in vacuo. Isolated yield: 0.62 g (82%), yellow oilHPLC: 97.4% purity | |
In acetone; at 20℃; for 1.5h;Product distribution / selectivity; | Example 11; Synthesis of the compound (I-R); [0074] 1.0 g 3-(l-(Dimethylamino)ethyl) phenol was dissolved in 20 ml acetone.[0075] 2.21 g bis(4-nitrophenyl)carbonate was added. The yellow solution was stirred at ambient temperature.[0076] Reaction progress was monitored with HPLC. After 1.5 hour, 537 mg N- ethylmethylamine was added dropwise and the yellow solution was stirred at ambient temperature for 1.5 hour. The reaction mixture was concentrated in vacuo. To the resulting yellow oil, 20 ml t-butylmethyl ether and 20 ml of a solution of hydrochloric acid (2 M) were added. The 2-phase system was stirred for 15 minutes. The acidic aqueous layer was washed with 20 ml t-butylmethyl ether.[0077] 20 ml t-Butylmethyl ether was added to the aqueous layer and a solution of sodium hydroxide (2 M) was added until pH~12 was reached. The organic layer was washed with 2x20 ml water, dried (Na2SO4), filtered and concentrated in vacuo.Isolated yield: 1.34 g (88%), yellow oilHPLC: 95.6% purity |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 4-methyl-morpholine; In dichloromethane; at 20℃; for 42h; | To a solution of the (6-methyl-pyridin-3-yl)-methanol in DCM (180 mL) was added bis-(4- nitrophenyl)carbonate (10.4 g, 34 mmol) followed by NMM (3.75 mL, 34 mmol). The reaction mixture was stirred at r.t. for 42 hours and then concentrated in vacuo. The residue <n="26"/>- -was dissolved in DCM (100 mL), washed with sat aq NaHCCh solution (6 x 100 mL), dried (MgSO4) and concentrated in vacuo. The crude product was recrystallised from EtOAc to give (6-methylpyridin-3-yl)methyl 4-nitrophenyl carbonate (7.38 g, 77%) as an orange solid. Analytical LCMS: (System A, RT = 1.74 min), ES+: 289.4 [MH]+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With 4-methyl-morpholine; In dichloromethane; at 20℃; for 48h; | To a solution of <strong>[5344-27-4]4-(2-hydroxyethyl)pyridine</strong> (0.25 mL, 2.2 mmol) in DCM (10 mL) was added bis-(/?-nitrophenyl)carbonate (0.67 g, 2.2 mmol) and NMM (0.24 mL, 2.2 mmol). The reaction mixture was stirred at r.t. for 2 days and then concentrated in vacuo to give an orange oil. The oil was dissolved in EtOAc (30 mL), washed with sat aq NaHCO3 solution (3 x 20 mL), dried (MgSO4) and concentrated in vacuo to give 4-nitrophenyl 2-(pyridin-4- yl)ethyl carbonate as an oil which was used without further purification in the next step. <n="32"/>- -To a solution of 4-nitrophenyl 2-(pyridin-4-yl)ethyl carbonate (~2.2 mmol) in DMF (10 mL) was added DIPEA (0.383 mL, 2.2 mmol) and c-2,6-dimethylmorpholine (0.27 mL, 2.2 mmol). The reaction mixture was stirred overnight at r.t. and then concentrated in vacuo. The residue was purified by normal phase chromatography (gradient eluting with MeOH in DCM from 0% to 2%) followed by reverse phase chromatography to give 2- pyridin-4-ylethyl (2R,6S)-2,6-dimethylmorpholine-4-carboxylate (128 mg, 22%) as a light yellow oil.Analytical HPLC: purity 99.6% (System B, Rtau = 3.44 min); Analytical LCMS: purity 100% (System F, Rtau = 5.18 min), ES+: 265.6 [MH]+; HRMS calcd for Ci4H20N2O3: 264.1474, found 264.1480. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With dmap; In dichloromethane; at 20℃; for 12.0h; | EXAMPLE 1.3. Synthesis of an M3 type compound of substituent 1 (8 in this Example); The carbonate 7 was prepared by reacting the disulfide 4 with bis(4-nitrophenyl) carbonate (Fardis, M.; Pyun, H.-J.; Tario, J.; Jin, H.; Kim, C. U.; Ruckman, J.; Lin, Y.; Green, L.; Hicke, B. Bioorg. Med. Chem. 2003, 11, 5051-5058.). Treatment of paclitaxel with 7 gave the M3 type paclitaxel disulfide 8 (Liu, C; Schilling, J. K.; Ravindra, R.; Bane, S.; Kingston, D. G. I. Bioorg. Med. Chem. 2004, 12, 6147-6161.); Synthesis of compound 8.; A solution of the disulfide 4 (see Senter, P. D.; Pearce, W. E.; Greenfield, R. S. /. Org Chem. 1990, 55, 2975-2978) (7 mg, 28 mumol) in dry dichloromethane (2 mL) was added to a stirred solution of bis(4-nitrophenyl) carbonate (12.8 mg, 42 mumol) and 4-(dimethylamino) pyridine (10.3 mg, 84 mumol) in dry <n="54"/>dichloromethane (2 mL). After being stirred at room temperature for 12 h, paclitaxel (47.8 mg, 56 mumol) was added. The reaction mixture was allowed to stir at room temperature for another 12 h (see Fardis, M.; Pyun, H.-J.; Tario, J.; Jin, H.; Kim, C. U.; Ruckman, J.; Lin, Y.; Green, L.; Hicke, B. Bioorg. Med. Chem. 2003, 11, 5051-5058; Liu, C; Schilling, J. K.; Ravindra, R.; Bane, S.; Kingston, D. G. I. Bioorg. Med. Chem. 2004, 12, 6147-6161.) Workup as described above and purification by preparative TLC (30% EtOAc/hexanes) afforded compound 8 (25.3 mg, 80%): 1H NMR (CDCl3). delta 8.48 (IH, d, / = 4.6 Hz), 8.13 (2H, d, J = 8.0 Hz), 7.71 (2H, d, / = 8.3 Hz), 7.25-7.65 (17H, m), 7.13 (IH, br dd, / = 5.1, 3.3 Hz), 6.88 (IH, d, J = 9.2 Hz), 6.29 (2H, br s), 5.97 (IH, br d, / = 9.2 Hz), 5.68 (IH, d, / = 7.0 Hz), 5.42 (IH, br s), 5.13 (IH, d, / = 12.3 Hz), 5.09 (IH, d, / = 12.3 Hz), 4.97 (IH, d, / = 9.4 Hz), 4.43 (IH, dd, J = 10.6, 6.9 Hz), 4.31 (IH, d, / = 8.5 Hz), 4.20 (IH, d, / = 8.5 Hz), 3.80 (IH, d, J = 7.0 Hz), 2.56 (IH, m), 2.44 (3H, s), 2.39 (IH, dd, J = 15.4, 9.4 Hz), 2.23 (3H, s), 2.19 (IH, dd, J = 15.4, 8.7 Hz), 1.91 (3H, s), 1.88 (IH, m), 1.68 (3H, s), 1.25 (3H, s), 1.13 (3H, s); 13C NMR (CDCl3) delta 203.8, 171.3, 169.8, 167.8, 167.1, 167.1, 159.2,154.0, 149.6, 142.6, 137.4, 136.6, 133.6, 133.4, 133.4, 132.8, 132.1, 130.2, 129.1, 129.1,129.1, 128.7, 128.7, 128.5, 127.4, 127.1, 126.5, 121.1, 119.8, 84.4, 81.1, 79.2, 77.2, 76.9, 76.4, 75.6, 75.1, 72.1, 72.1, 70.0, 58.5, 52.7, 45.6, 43.2, 35.6, 35.6, 26.8, 22.7, 22.2, 20.8, 14.8, 9.6; HRFABMS m/z 1129.3433 [M + H+] (calcd for C60H6IN2Oi6S2, 1129.3463). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | With N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; for 3h; | 2-(2,5-dioxo-2,5-dihydro-1 H-pyrrol-1-yl)ethyl (4-nitrophenyl) carbonate To a solution of 1-(2-hydroxyethyl)-1 H-pyrrole-2,5-dione (250 mg, 1.77 mmol) in DCM (8.9 ml) was added diisopropylethylamine (1.5 ml, 8.86 mmol) and bis(4-nitrophenyl) carbonate (701 mg, 2.30 mmol) and the reaction mixture was stirred at RT for 3h. The reaction was extracted with water and DCM. The organic layers were combined, dried over Na2S04, filtered and concentrated to dryness. Purification of the crude product by chromatography on silica eluting with 0 - 100percent EtOAc in heptane afforded the title compound as a pale yellow solid in 88percent yield; H-NMR (DMSO, 400 MHz): delta 8.34-8.32 (2H, m), 7.54-7.51 (2H, m), 7.09 (2H, s), 4.36-4.34 (2H, m), 3.81-3.79 (2H, m). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
1.1 g | To a solution of intermediate 4 (785 mg, 0.739 mmol) in DMF (3695 mul) was added bis(4-nitrophenyl) carbonate (337 mg, 1.108 mmol) and DIPEA (193 mul, 1.108 mmol). The reaction was stirred at RT for 1.5 h. To the mixture was then added <strong>[134272-64-3]1-(2-aminoethyl)-1H-pyrrole-2,5-dione hydrochloride</strong> (261 mg, 1.478 mmol) and DIPEA (386 muL, 2.217 mmol). The resulting solution was stirred at RT for 30 min before it was added to Et2O (50 mL). The resulting precipitate was collected by vacuum filtration, washing with Et2O (2*5 mL), to provide allyl N2-acetyl-N5-((S)-1-(((S)-1-((2-(((S)-6-((tert-butoxycarbonyl)amino)-1-((4-((((2-(2,5-dioxo-2,5-dihydro-1H-pyrrol-1-yl)ethyl)carbamoyl)oxy)methyl)phenyl)amino)-1-oxohexan-2-yl)amino)-2-oxoethyl)amino)-1-oxo-3-(trityloxy)propan-2-yl)amino)-4-methyl-1-oxopentan-2-yl)-L-glutaminate (1.1 g). MS(ESI+) m/z 1228.7 (M+H)+. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
78% | To a solution of intermediate 12 (69 mg, 0.050 mmol) in DMF (251 mul) was added bis(4-nitrophenyl) carbonate (22.92 mg, 0.075 mmol) and DIPEA (13.12 mul, 0.075 mmol). The reaction was stirred at RT for 1 h before <strong>[134272-64-3]1-(2-aminoethyl)-1H-pyrrole-2,5-dione hydrochloride</strong> (17.74 mg, 0.100 mmol) and DIPEA (26.2 mul, 0.151 mmol) was added. The resulting mixture was stirred at RT for an additional 1 h and was then added, dropwise, to a vial of Et2O (15 mL). The resulting precipitate was collected by vacuum filtration, washed with Et2O (3×3 mL), and dried under vacuum to provide compound 13 (60 mg, 78%). MS(ESI+) m/z 1539.8 (M+H)+. |