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CAS No. : | 120205-50-7 | MDL No. : | MFCD18157735 |
Formula : | C14H25NO5 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | LNEHHTWYEBGHBY-OUAUKWLOSA-N |
M.W : | 287.35 | Pubchem ID : | 11033491 |
Synonyms : |
|
Num. heavy atoms : | 20 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.86 |
Num. rotatable bonds : | 7 |
Num. H-bond acceptors : | 5.0 |
Num. H-bond donors : | 1.0 |
Molar Refractivity : | 78.68 |
TPSA : | 76.07 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.88 cm/s |
Log Po/w (iLOGP) : | 2.79 |
Log Po/w (XLOGP3) : | 1.65 |
Log Po/w (WLOGP) : | 1.74 |
Log Po/w (MLOGP) : | 1.03 |
Log Po/w (SILICOS-IT) : | 1.03 |
Consensus Log Po/w : | 1.65 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.56 |
Log S (ESOL) : | -2.2 |
Solubility : | 1.82 mg/ml ; 0.00632 mol/l |
Class : | Soluble |
Log S (Ali) : | -2.86 |
Solubility : | 0.396 mg/ml ; 0.00138 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -0.97 |
Solubility : | 30.4 mg/ml ; 0.106 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 0.0 |
Synthetic accessibility : | 3.85 |
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 |
---|---|---|
100% | With diethyl cyanophosphonate; triethylamine; In DMF (N,N-dimethyl-formamide); at 0 - 20℃; for 75h; | [0304] In following the procedure of Shioiri et al. (Shioiri, T.; Hayashi, K.; Hamada, Y. Tetrahedron. 49(9), 1993, 1913-1924), a solution of (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethylamine (0.20 g, 1.0 mmol, from Reference Example 4) and <strong>[120205-50-7](2R,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methylpropanoic acid</strong> (0.28 g, 1.0 mmol) in anhydrous dimethylformamide (3 mL) is cooled to 0 C. (ice-water bath) while stirring under a nitrogen atmosphere. Diethyl cyanophosphonate (0.16 mL, 1.05 mmol) is added dropwise via syringe, followed by triethylamine (0.14 mL, 1.0 mmol). Stirring is continued for two hours at room temperature and then at room temperature for three days. The reaction mixture is diluted with 30 mL of ethyl acetate/toluene (2:1) and washed with 1 M aqueous potassium bisulfate solution, water, saturated aqueous sodium bicarbonate solution, and saturated aqueous sodium chloride solution. The organic phase is dried over anhydrous sodium sulfate, decanted, and concentrated under reduced pressure to give 0.47 g (100%) of Boc-(2R,3R,4S)-dolaproine-(S)-dolaphenine as a light yellow foam. |
81% | With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; | Compound 1J: tert-butyl (2S)-2-[( 1 R,2R)- 1 -methoxy-2-methyl-2-[ [(1 S)-2- phenyl- 1 -(1 ,3-thiazo l-2-yl)ethyl]carbamoyl]ethyl]pyrro lidine- 1 -carboxylate Compound 1 (3 g, 9.86 mmol, 1.00 equiv) was dissolved in an inert atmosphere in 10 mL DCM. Trifluoroacetic acid (TFA, 10 mL) was added and the solution left under agitation overnight at ambient temperature, then concentrated under reduced pressure to yield 2.0 g (64 %) of (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethan-1-amine; trifluoroacetic acid in the form of a yellow oil. This intermediate was re-dissolved in 20mL of DCM after which compound 1D (1.8 g, 6.26 mmol, 1.05 equiv), DEPC (1.1 g,6.75 mmol, 1.13 equiv) and diisopropylethylamine (DIEA, 1.64 g, 12.71 mmol, 2.13 equiv) were added. The reaction mixture was left under agitation overnight at ambient temperature, then concentrated under reduced pressure. The residue was purified on a silica colunm with a mixture of EtOAc and PE (1:100 to 1:3) to yield 2.3 g (81 %) ofcompound 1J in the form of a pale yellow solid. |
81% | With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃;Inert atmosphere; | Compound II (3 g, 9.86 mmol, 1.00 equiv) was dissolved in an inert atmosphere in 10 mL DCM. Trifluoroacetic acid (TFA, 10 mL) was added and the solution left under agitation overnight at ambient temperature, then concentrated under reduced pressure to yield 2.0 g (64 %) of (l S)-2-phenyl-l-(l ,3-thiazol-2-yl)ethan-l-amine; trifluoroacetic acid in the form of a yellow oil. This intermediate was re-dissolved in 20 mL of DCM after which compound ID (1.8 g, 6.26 mmol, 1.05 equiv), DEPC (1.1 g, 6.75 mmol, 1.13 equiv) and diisopropylethylamine (DIEA, 1.64 g, 12.71 mmol, 2.13 equiv) were added. The reaction mixture was left under agitation overnight at ambient temperature, then concentrated under reduced pressure. The residue was purified on a silica column with a mixture of EtOAc and PE (1 : 100 to 1 :3) to yield 2.3 g (81 %) of compound 1 J in the form of a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With diethyl cyanophosphonate; triethylamine; In N,N-dimethyl-formamide; at 0 - 20℃; for 20h; | To a solution of 11 (280 mg, 0.974 mmol, 1 eq.) and 15 (460 mg, 1.44 mmol, 1.48 eq.) in NN- dimethylformamide (3 mL, 0.32 M) at 0 C was added diethylphosphoryl cyanide (DEPC) (93% purity, 212 muEpsilon, 1.30 mmol, 1.34 eq.), followed by triethylamine (367 2.63 mmol, 2.7 eq.). After 2 hours at 0 C, the reaction mixture was warmed to room temperature for 18 hours. The reaction mixture was then diluted with ethyl acetate:toluene (2: 1, 30 mL) and was washed successively with 1 M aqueous sodium bisulfate solution (35 mL) and 50% saturated aqueous sodium bicarbonate solution (4 x 25 mL). The organic layer was dried over sodium sulfate, filtered, concentrated in vacuo, and purified by silica gel chromatography (12% to 100% ethyl acetate in heptane) to give 16 as a light amber oil (374 mg, 81%). LC-MS: m/z 474.4 [M+H+], 374.4 [(M - 2-methylprop-l-ene)+H+] retention time = 3.63 minutes; H NMR (400 MHz, DMSO-i), characteristic signals: delta 8.66 (d, J=8.5 Hz, IH), 7.78 (d, J=3.3 Hz, IH), 7.64 (d, J=3.3 Hz, IH), 7.21-7.31 (m, 4H), 7.14-7.20 (m, IH), 5.40 (ddd, J=1 1.4, 8.5, 4.0 Hz, IH), 3.23 (br s, 3H), 2.18 (dq, J=9.7, 6.7 Hz, IH), 1.06 (d, J=6.6 Hz, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
81% | With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; | Compound 1 (3 g, 9.86 mmol, 1.00 equiv) was dissolved in an inert atmosphere in 10 mL DCM. Trifluoroacetic acid (TFA, 10 mL) was added and the solution leftunder agitation overnight at ambient temperature, then concentrated under reduced pressure to yield 2.0 g (64 %) of (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethan-1-amine; trifluoroacetic acid in the form of a yellow oil. This intermediate was re-dissolved in 20 mL of DCM after which compound 1D (1.8 g, 6.26 mmol, 1.05 equiv), DEPC (1.1 g, 6.75 mmol, 1.13 equiv) and diisopropylethylamine (DIEA, 1.64 g, 12.71 mmol, 2.13equiv) were added. The reaction mixture was left under agitation overnight at ambient temperature, then concentrated under reduced pressure. The residue was purified on a silica colunm with a mixture of EtOAc and PE (1:100 to 1:3) to yield 2.3 g (81 %) of compound 1J in the form of a pale yellow solid. |
81% | With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; | Compound 1 (3 g, 9.86 mmol, 1.00 equiv) was dissolved in an inert atmosphere in 10 mL DCM. Trifluoroacetic acid (TFA, 10 mL) was added and the solution leftunder agitation overnight at ambient temperature, then concentrated under reduced pressure to yield 2.0 g (64 %) of (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethan-1-amine; trifluoroacetic acid in the form of a yellow oil. This intermediate was re-dissolved in 20 mL of DCM after which compound 1D (1.8 g, 6.26 mmol, 1.05 equiv), DEPC (1.1 g, 6.75 mmol, 1.13 equiv) and diisopropylethylamine (DIEA, 1.64 g, 12.71 mmol, 2.13equiv) were added. The reaction mixture was left under agitation overnight at ambient temperature, then concentrated under reduced pressure. The residue was purified on a silica colunm with a mixture of EtOAc and PE (1:100 to 1:3) to yield 2.3 g (81 %) of compound 1J in the form of a pale yellow solid. |
81% | With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; | Compound 1 (3 g, 9.86 mmol, 1.00 equiv) was dissolved in an inert atmosphere in 10 mL DCM. Trifluoroacetic acid (TFA, 10 mL) was added and the solution leftunder agitation overnight at ambient temperature, then concentrated under reduced pressure to yield 2.0 g (64 %) of (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethan-1-amine; trifluoroacetic acid in the form of a yellow oil. This intermediate was re-dissolved in 20 mL of DCM after which compound 1D (1.8 g, 6.26 mmol, 1.05 equiv), DEPC (1.1 g, 6.75 mmol, 1.13 equiv) and diisopropylethylamine (DIEA, 1.64 g, 12.71 mmol, 2.13equiv) were added. The reaction mixture was left under agitation overnight at ambient temperature, then concentrated under reduced pressure. The residue was purified on a silica colunm with a mixture of EtOAc and PE (1:100 to 1:3) to yield 2.3 g (81 %) of compound 1J in the form of a pale yellow solid. |
81% | With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; | Compound 1J: tert-butyl (2S)-2-[(1R,2R)-1-methoxy-2-methyl-2-[[(1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethyl]carbamoyl]ethyl]pyrrolidine-1-carboxylate Compound 1I (3 g, 9.86 mmol, 1.00 equiv) was dissolved in an inert atmosphere in 10 mL DCM. Trifluoroacetic acid (TFA, 10 mL) was added and the solution left under agitation overnight at ambient temperature, then concentrated under reduced pressure to yield 2.0 g (64%) of (1S)-2-phenyl-1-(1,3-thiazol-2-yl)ethan-1-amine; trifluoroacetic acid in the form of a yellow oil. This intermediate was re-dissolved in 20 mL of DCM after which compound 1D (1.8 g, 6.26 mmol, 1.05 equiv), DEPC (1.1 g, 6.75 mmol, 1.13 equiv) and diisopropylethylamine (DIEA, 1.64 g, 12.71 mmol, 2.13 equiv) were added. The reaction mixture was left under agitation overnight at ambient temperature, then concentrated under reduced pressure. The residue was purified on a silica column with a mixture of EtOAc and PE (1:100 to 1:3) to yield 2.3 g (81%) of compound 1J in the form of a pale yellow solid. |
81% | With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; at 20℃; | Compound 1 (3 g, 9.86 mmol, 1.00 equiv) was dissolved in an inert atmosphere in 10 mL DCM. Trifluoroacetic acid (TFA, 10 mL) was added and the solution left under agitation overnight at ambient temperature, then concentrated under reduced pressure to yield 2.0 g (64 %) of (1 S)-2-phenyl- 1 -(1 ,3-thiazo l-2-yl)ethan- 1-amine; trifluoroacetic acid in theform of a yellow oil. This intermediate was re-dissolved in 20 mL of DCM after which compound 1D (1.8 g, 6.26 mmol, 1.05 equiv), DEPC (1.1 g, 6.75 mmol, 1.13 equiv) and diisopropylethylamine (DIEA, 1.64 g, 12.71 mmol, 2.13 equiv) were added. The reaction mixture was left under agitation overnight at ambient temperature, then concentrated under reduced pressure. The residue was purified on a silica colunm with a mixture of EtOAc andPE (1:100 to 1:3) to yield 2.3 g (81 %) of compound 1J in the form of a pale yellow solid. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
To 10 (25.0 g, 92.8 mmol, 1 eq.) in tert-butanol (100 mL, 0.93 M) was immediately added water (30.00 mL) followed by N-methylmorpholine-N-oxide (25.97 g, 192.1 mmol, 2.07 eq.) and osmium tetroxide (235.93 mg, 928.04 muetaiotaomicron, 0.01 eq.) After 12 hours, the mixture was concentrated in vacuo using water (20 mL) to azeotropically remove residual ferZ-butanol. The residue was partitioned between ethyl acetate (500 mL) and water (500 mL) plus brine (150 mL). The aqueous layer was re-extracted with ethyl acetate (250 mL). The combined organic layers were washed with aqueous sodium chloride solution (10 wt%, 200 mL), washed with water (150 mL), and concentrated in vacuo to afford a water-wet pale brown oil that was re-concentrated from ethyl acetate (100 mL) to remove any remaining water. This crude diol (34.76 g) was used without further purification. To the crude diol (34.76 g, <92.8 mmol, 1 eq.) in acetonitrile (347 mL, 0.1 M) and water (174 mL) was added sodium permanganate (2.03 g, 5.73 mmol, 0.05 eq.). The mixture was cooled to 0 C and sodium periodate (51.46 g, 240.6 mmol, 2.1 eq.) was added portion- wise over 30 minutes, while keeping the internal temperature below 5 C. The reaction was stirred at 0 C for 4 hours and was then poured into a solution of sodium thiosulfate pentahydrate (65.40 g, 263.5 mmol, 2.3 eq.) in water (100 mL). The mixture was filtered through Celite and the filtrate was concentrated in vacuo. The residue was partitioned between ethyl acetate (200 mL) and water (200 mL). The aqueous layer was back-extracted with ethyl acetate (250 mL), and the combined organic layers were washed with a 10% aqueous citric acid solution. As the desired product was very soluble in water, all the aqueous layers were combined, treated with Celite (100 g) and concentrated in vacuo to yield an off-white paste. Ethyl acetate (150 mL) was added and the mixture was re-concentrated to remove any residual water; this operation was repeated one more time. The paste was treated with ethyl acetate (150 mL) and placed in vacuo at 50 C for 10 minutes and filtered (repeated twice). These filtrates were combined with the previous organic layer (from the citric acid wash), concentrated, diluted with ethyl acetate (200 mL) and filtered through Celite to remove solids. Finally, this filtrate was concentrated to yield 11 (22.9 g, 69% over two steps) as a yellowish/brown foam. LCMS (Protocol I): m/z 310.1 [M+Na+], 232.1 [(M - 2-methylprop-l-ene)+H+], 188.1 [(M - Boc)+H+], retention time = 3.268 minutes; NMR (400 MHz, DMSO-i), characteristic signals: delta 3.61-3.85 (br m, 2H), 3.20-3.45 (br m, 4H), 3.03-3.17 (br m, 1H), 1.59-1.93 (br m, 4H), 1.40 (br s, 9H), 1.02-1.18 (br m, 3H). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | 300 mg of intermediate (IV) was dissolved in 6ml of tetrahydrofuran, cooled to 0 C, 0.2 g of sodium hydride was added, Stirred for 30 minutes, added with 1.2 ml of methyl iodide and continued stirring at 0 C overnight. The reaction was monitored by TLC. After completion of the reaction, quench the reaction by adding 15 ml of waterShould be spinned tetrahydrofuran, washed once with ethyl acetate, water phase, the use of hydrochloric acid adjusted rhoEta = 3, extracted with 15ml of ethyl acetatethree timesThe combined organics were spin-dried and chromatographed with petroleum ether: ethyl acetate 6: 1. That is, Dap (289 mg, 91%) | |
72% | [0303] In following the procedure of Shioiri et al. (Shioiri, T.; Hayashi, K.; Hamada, Y. Tetrahedron. 49(9), 1993, 1913-1924), to a solution of (2R,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-hydroxy-2-methylpropanoic acid (0.56 g, 2.0 mmol) in tetrahydrofuran (10 mL) is added iodomethane (1.9 mL, 30 mmol). The mixture is cooled to 0 C. (ice-water bath) while stirring under a nitrogen atmosphere. Sodium hydride (60% dispersion in mineral oil, 0.32 g, 8.0 mmol) is added in portions to keep the reaction mixture from frothing excessively. Stirring is continued for 2 hours at 0 C. and then the reaction vessel is stored for 3 days in a -5 C. freezer. The mixture is quenched by the addition of saturated aqueous sodium bicarbonate solution (20 mL) and then extracted with ether to remove impurities and mineral oil. The basic aqueous phase is acidified to pH 2 with 1 M potassium bisulfate solution and then extracted twice with ethyl acetate. The combined extracts are washed with 5% aqueous sodium thiosulfite solution and saturated aqueous sodium chloride solution, dried over anhydrous sodium sulfite, and concentrated under reduced pressure to give (2R,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methylpropanoic acid (Boc-(2R,3R,4S)-dolaproine) as a clear, colorless semisolid (0.41 g, 72%). lbut-2-enyl]-N1,3-dimethyl-L-valinamide (94 mg, 0.20 mmol, WO 99/32509) and (2R,3R,4S)-dolaproine-(S)-dolaphenine (66 mg, 0.18 mmol) in anhydrous dimethylformamide (1 mL) are reacted with diethyl cyanophosphonate (33 muL, 0.22 mmol) in the presence of triethylamine (31 muL, 0.22 mmol). After stirring for 2 days, the reaction mixture is quenched with a few drops of water and immediately purified by reverse-phase HPLC (Prodigy ODS3 column, acetonitrile/water/trifluoroacetic acid) to give the title compound as a TFA salt (84 mg). MS (ES+): (M+H) 829.6 | |
72% | With sodium hydride; In tetrahydrofuran; mineral oil; at 0℃; for 72h;Inert atmosphere; | Compound 1C (7.31 g, 26.74 mmol, 1.00 equiv) was dissolved in an inert atmosphere in THF (135 mL) in the presence of iodomethane (25.3 mL). The reaction medium was cooled with an ice bath after which NaH (60 % in oil, 4.28 g) was added inportions. The reaction was left under agitation 3 days at 0C and then neutralised with100 mL of sodium bicarbonate saturated aqueous solution and washed 3 times with50 mL ether. The pH of the aqueous solution was adjusted to 3 with 1M aqueousKHSO4 solution. This aqueous solution was extracted 3 times with 100 mL of EtOAc.The organic phases were combined, washed once with 100 mL of Na2S2O3 (5 % in water), once with NaCl-saturated solution, then dried over sodium sulfate, filtered and concentrated to yield 5.5 g (72 %) of compound 1D in the form of a colourless oil. |
72% | With sodium hydride; In tetrahydrofuran; mineral oil; at 0℃; for 72h;Inert atmosphere; | Compound 1C (7.31 g, 26.74 mmol, 1.00 equiv) was dissolved in an inert atmosphere in THF (135 mL) in the presence of iodomethane (25.3 mL). The reaction medium was cooled with an ice bath after which NaH (60 % in oil, 4.28 g) was added inportions. The reaction was left under agitation 3 days at 0C and then neutralised with100 mL of sodium bicarbonate saturated aqueous solution and washed 3 times with50 mL ether. The pH of the aqueous solution was adjusted to 3 with 1M aqueousKHSO4 solution. This aqueous solution was extracted 3 times with 100 mL of EtOAc.The organic phases were combined, washed once with 100 mL of Na2S2O3 (5 % in water), once with NaCl-saturated solution, then dried over sodium sulfate, filtered and concentrated to yield 5.5 g (72 %) of compound 1D in the form of a colourless oil. |
72% | With sodium hydride; In tetrahydrofuran; mineral oil; at 0℃; for 72h;Inert atmosphere; | Compound 1C (7.31 g, 26.74 mmol, 1.00 equiv) was dissolved in an inert atmosphere in THF (135 mL) in the presence of iodomethane (25.3 mL). The reaction medium was cooled with an ice bath after which NaH (60 % in oil, 4.28 g) was added inportions. The reaction was left under agitation 3 days at 0C and then neutralised with100 mL of sodium bicarbonate saturated aqueous solution and washed 3 times with50 mL ether. The pH of the aqueous solution was adjusted to 3 with 1M aqueousKHSO4 solution. This aqueous solution was extracted 3 times with 100 mL of EtOAc.The organic phases were combined, washed once with 100 mL of Na2S2O3 (5 % in water), once with NaCl-saturated solution, then dried over sodium sulfate, filtered and concentrated to yield 5.5 g (72 %) of compound 1D in the form of a colourless oil. |
72% | With sodium hydride; In tetrahydrofuran; mineral oil; at 0℃; for 72h;Inert atmosphere; Cooling with ice; | Compound 1D: (2R,3R)-3-[(2S)- 1 -[(tert-butoxy)carbonyl]pyrrolidin-2-yl]- 3-methoxy-2-methylpropanoic acid Compound 1C (7.31 g, 26.74 mmol, 1.00 equiv) was dissolved in an inert atmosphere in THF (135 mL) in the presence of iodomethane (25.3 mL). The reaction medium was cooled with an ice bath after which NaH (60 % in oil, 4.28 g) was added in portions. The reaction was left under agitation 3 days at 0C and then neutralised with100 mL of sodium bicarbonate saturated aqueous solution and washed 3 times with 50 mL ether. The pH of the aqueous solution was adjusted to 3 with 1M aqueous KHSO4 solution. This aqueous solution was extracted 3 times with 100 mL of EtOAc. The organic phases were combined, washed once with 100 mL of Na2S2O3 (5 % in water), once with NaC1-saturated solution, then dried over sodium sulfate, filtered andconcentrated to yield 5.5 g (72 %) of compound 1D in the form of a colourless oil. |
72% | With sodium hydride; In tetrahydrofuran; mineral oil; at 0℃; for 72h;Inert atmosphere; | Compound ID: (2R,3R)-3-[(2S)-l-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]- 3-methoxy- -methylpropanoic acid Compound 1C (7.31 g, 26.74 mmol, 1.00 equiv) was dissolved in an inert atmosphere in THF (135 mL) in the presence of iodomethane (25.3 mL). The reaction medium was cooled with an ice bath after which NaH (60 % in oil, 4.28 g) was added in portions. The reaction was left under agitation 3 days at 0C and then neutralised with 100 mL of sodium bicarbonate saturated aqueous solution and washed 3 times with 50 mL ether. The pH of the aqueous solution was adjusted to 3 with 1M aqueous KHSO4 solution. This aqueous solution was extracted 3 times with 100 mL of EtOAc. The organic phases were combined, washed once with 100 mL of Na2S203 (5 % in water), once with NaCl-saturated solution, then dried over sodium sulfate, filtered and concentrated to yield 5.5 g (72 %) of compound ID in the form of a colourless oil. |
72% | With sodium hydride; In tetrahydrofuran; mineral oil; at 0℃; for 72h;Inert atmosphere; | Compound 1C (7.31 g, 26.74 mmol, 1.00 equiv) was dissolved in an inert atmosphere in THF (135 mL) in the presence of iodomethane (25.3 mL). The reaction medium was cooled with an ice bath after which NaH (60 % in oil, 4.28 g) was added in portions. The reaction was left under agitation 3 days at 0C and then neutralised with 100 mL of sodium bicarbonate saturated aqueous solution and washed 3 times with 50 mL ether. The pH of the aqueous solution was adjusted to 3 with 1M aqueous KHSO4 solution. This aqueous solution was extracted 3 times with 100 mL of EtOAc. The organic phases were combined, washed once with 100 mL of Na2S2C>3 (5 % in water), once with NaCl-saturated solution, then dried over sodium sulfate, filtered and concentrated to yield 5.5 g (72 %) of compound ID in the form of a colourless oil. |
72% | With sodium hydride; In tetrahydrofuran; mineral oil; at 0℃; for 72h;Inert atmosphere; | Compound 1D: (2R,3R)-3-[(2S)-1-[(tert-butoxy)carbonyl]pyrrolidin-2-yl]-3-methoxy-2-methylpropanoic acid Compound 1C (7.31 g, 26.74 mmol, 1.00 equiv) was dissolved in an inert atmosphere in THF (135 mL) in the presence of iodomethane (25.3 mL). The reaction medium was cooled with an ice bath after which NaH (60% in oil, 4.28 g) was added in portions. The reaction was left under agitation 3 days at 0 C. and then neutralised with 100 mL of sodium bicarbonate saturated aqueous solution and washed 3 times with 50 mL ether. The pH of the aqueous solution was adjusted to 3 with 1M aqueous KHSO4 solution. This aqueous solution was extracted 3 times with 100 mL of EtOAc. The organic phases were combined, washed once with 100 mL of Na2S2O3 (5% in water), once with NaCl-saturated solution, then dried over sodium sulfate, filtered and concentrated to yield 5.5 g (72%) of compound 1D in the form of a colourless oil. |
72% | With sodium hydride; In tetrahydrofuran; mineral oil; at 0℃; for 72h;Inert atmosphere; | Compound 1C (7.31 g, 26.74 mmol, 1.00 equiv) was dissolved in an inert atmosphere in THF (135 mL) in the presence of iodomethane (25.3 mL). The reaction medium wascooled with an ice bath after which NaH (60 % in oil, 4.28 g) was added in portions. The reaction was left under agitation 3 days at 0C and then neutralised with 100 mL of sodium bicarbonate saturated aqueous solution and washed 3 times with 50 mL ether. The pH of the aqueous solution was adjusted to 3 with 1M aqueous KHSO4 solution. This aqueous solution was extracted 3 times with 100 mL of EtOAc. The organic phases were combined, washedonce with 100 mL of Na2S2O3 (5 % in water), once with NaC1-saturated solution, then dried over sodium sulfate, filtered and concentrated to yield 5.5 g (72 %) of compound 1D in the form of a colourless oil. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
98% | Exam le 6 Preparation of compound 8 To a solution of 7 (1.80 g, 4.03 mmol) in THF (30 mL) and Q (7.5 mL), 30% 02 (1 .44 mL, 14.4 mmoi) was added over a 5 min period at 0 C , followed by a solution of LiOH (0.27 g, 6.45 mmol) in water (5 mL). After stirring at 0 C for 3 h, 1 N sodium sulfite (15.7 mL) was added and the mixture was allowed to warm to r.t. and stirred overnight. THF was removed in vacuo and the aqueous phase was wash with dichloromethane (3 x 50 mL) to remove the oxazoiidmone auxiliary. The aqueous phase was acidified to pH 3 with IN HC1 and extracted with ethyl acetate (3 x 50 mL). The organic layer was washed with brine (50 mL), dried over Na2S04, filtered and concentrated in vacuo to afford the compound 8 as a colorless oil (1.15 g, 98% yield). 1H NMR (500 MHz, CDC13) delta 3.99 - 3.74 (m, 2H), 3.44 (d, J = 2.6 Hz, 3H), 3.23 (s, 1H), 2.60 - 2.45 (m, 1H), 1.92 (tt, J = 56.0, 31.5 Hz, 3H), 1.79 - 1.69 (m, 1H), 1.58 - 1.39 (m, 9H), 1.30 - 1.24 (m, 3H). | |
98% | With dihydrogen peroxide; lithium hydroxide; In tetrahydrofuran; water; at 0℃; for 3h; | Example 28. (2R,3R)-3 -((S )- 1 -(tert-butoxycarbonyl)pyrrolidin-2-yl)-3 -methoxy-2- methylpropanoic acid ?l?o a solution of (5)-tert-butyl 2-(( 1R,2R)- 1 -methoxy-2-methyl-3-((4R,55)-4-methyl- 2-oxo-5-phenyloxazolidin-3-yl)-3-oxopropyl)pyrrolidine- 1 -carboxylate (1.80 g, 41)3mmoi) in T HF (30 mL) and H20 (7.5 mE), 30% f12O (1 .44 mU 14.4 mmoi) was added over a 5 mm period at 0 C , followed by a solution of LiOFI (0.27 g, 645 rrnnoi) in water (5 mL). After stining at 0 o for 3 h, I N sodium sulfite (153 niL) was added and the mixture was allowed to warm to r.t. and stirred overnight. TI-IF was removed in vacuo and the aqueous phase was wash with dichioromethane (3 x50 mL) to remove theoxazolidinone auxiliary. The aqueous phase was acidified to pH 3 with iN HG and extraded with ethyl acetate (3 x 50 mL). The organic layer was washed with brine (50 mL), dried over Na2504, filtered and concentrated in vacuo to afford the title compound as colorless oil (L15 g, 98% yield). ?H NMR (500 MHz, CDC13) oe 3.99 - 3.74 (m, 2H), 3.44 (d, J = 2.6 Hz, 3H), 3.23 (s, 1H), 2.60 - 2.45 (m, 1H), 1.92 (tt, J = 56.0, 31.5 Hz, 3H), 1.79- 1.69 (m, 1H), 1.58 - 1.39 (m, 9H), 1.30- 1.24 (m, 3H). |
98% | To a solution of 213 (1.80 g, 4.03 mmol) in THF (30 mL) and H2O (7.5 mL), 30% H2O2 (1.44 mL, 14.4 mmol) was added over a 5 min period at 0 C , followed by a solution of LiOH (0.27 g, 6.45 mmol) in water (5 mL). After stirring at 0 C for 3 h, 1 N sodium sulfite (15.7 mL) was added and the mixture was allowed to warm to r.t. and stirred overnight. THF was removed in vacuo and the aqueous phase was wash with dichloromethane (3 × 50 mL) to remove the oxazolidinone auxiliary. The aqueous phase was acidified to pH 3 with 1N HCl and extracted with ethyl acetate (3 × 50 mL). The organic layer was washed with brine (50 mL), dried over Na2SO4, filtered and concentrated in vacuo to afford the compound 214 as a colorless oil (1.15 g, 98% yield).1H NMR (500 MHz, CDCl3) ^ 3.99- 3.74 (m, 2H), 3.44 (d, J = 2.6 Hz, 3H), 3.23 (s, 1H), 2.60- 2.45 (m, 1H), 1.92 (tt, J = 56.0, 31.5 Hz, 3H), 1.79- 1.69 (m, 1H), 1.58- 1.39 (m, 9H), 1.30- 1.24 (m, 3H). |
98% | With dihydrogen peroxide; lithium hydroxide; In tetrahydrofuran; water; at 0℃; for 3h; | At 0 C,(S) -2-((1R, 2R) -1-methoxy-2-methyl-3-((4R, 5S) -4-methyl-2-oxo-5-phenyloxazolidin-3-yl) -3-Oxopropyl) pyrrolidine-1-carboxylic acid- (3) -oxopropyl) pyrrolidine-1-carboxylic acid tert-butyl ester(1.80g, 4.03mmol)Tetrahydrofuran (30 mL) andTo a solution of water (7.5 mL) was added 30% H2O2 (1.44 mL, 14.4 mmol).LiOH (0.27 g, 6.45 mmol) in water (5 mL) was then added.After stirring at 0 C for 3 hours,1N sodium sulfite (15.7 mL) was added and the mixture was warmed to room temperature and stirred overnight.Removal of tetrahydrofuran in vacuo,The aqueous phase was washed with dichloromethane (3 x 50 mL) and the oxazolidone auxiliary was removed. The aqueous phase was acidified to pH 3 with 1N hydrochloric acid and extracted with ethyl acetate (3 x 50 mL). The organic layer was washed with brine (50 mL), dried over anhydrous sodium sulfate, filtered, and concentrated under reduced pressure to give the title compound as a colorless oil (1.15 g, 98% yield). |
With lithium hydroxide monohydrate; water; dihydrogen peroxide; In tetrahydrofuran; at 0 - 30℃; for 12h;Inert atmosphere; | (S)-tert-butyl 2-((1R,2R)-1-methoxy-2-methyl-3-((4R,5S)-4-methyl-2-oxo-5-phenyloxazolidin-3-yl)-3 -oxopropyl)pyrrolidine-1-carboxylate 25c (1.3 g, 2.9 mmol) was dissolved in 80 mL of tetrahydrofuran. The solution was cooled to 0 C under argon atmosphere, and added with 30% hydrogen peroxide (1.25 g, 11 mmol) dropwise and lithium hydroxide monohydrate (207 mg, 4.95 mmol). The reaction mixture was stirred at room temperature for 12 hours. After completion of the reaction, sodium sulfite solid (1.47 g, 11.6 mmol) was added to the reaction solution, and the mixture was stirred at room temperature for 1 hour. A small amount of water was added and the organic phase was concentrated under reduced pressure. A small amount of water was added to dissolve the residues and extracted with dichloromethane (50 mL * 2). The aqueous phase was added with hydrochloric acid until pH= 3 and extracted with dichloromethane (40 mL * 3). The organic phase was washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate, filtered and the filtrate was concentrated under reduced pressure to give the crude title product of (2R,3R)-3-((S)-1-(tert-butoxycarbonyl)pyrrolidin-2-yl)-3-methoxy-2-methylpropanoic acid 25d (870 mg, colorless oil). The product was used in the next step without further purification. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | In methanol; diethyl ether; hexane; at 0 - 20℃; for 0.166667h; | [0307] To a 0 C. (ice-water bath) solution of <strong>[120205-50-7](2R,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methylpropanoic acid</strong> (0.20 g, 0.70 mmol, from Example 29) in methanol (2 mL) and diethyl ether (1 mL) is added trimethylsilyl diazomethane (2.0 M in hexanes, approx. 0.5-0.6 mL, Aldrich) until the yellow color of the reagent persisted. Then the reaction mixture is allowed to stir at room temperature for 10 minutes, after which the volatiles are removed under reduced pressure to a give 0.21 g (>100%) of crude methyl (2R,3R,2'S)-3-(N-tert-butoxycarbonyl-2'-pyrrolidinyl)-3-methoxy-2-methylpropanoate. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With N-ethyl-N,N-diisopropylamine; bromo-tris(1-pyrrolidinyl)phosphonium hexafluorophosphate; at 0 - 20℃; for 1.5h; | 3,4-Methylenedioxy-5,4 -dimethoxy-3 -(iValpha-Boc-L-Dap)-amido-Z-stilbene (13).To a stirred mixture of amine Ia (51 mg, 0.17 mmol), Lambda^-Boc-L-Dap 12 (52 mg, 0.18 mmol, 1.1 eq),32'33 and PyBroP (87 mg, 0.19 mmol, 1.1 eq) at 0 EC under Ar was added DIPEA (65 muL, 0.37 mmol, 2.2 eq). The reaction mixture was stirred for 1.5 h at rt. DCM (10 mL) was added, and the mixture was washed with aqueous citric acid (10% by wt, 10 mL). The organic layer was dried with magnesium sulfate and concentrated in vacuo, and the residue was subjected to gravity column chromatography (8:1, DCM-EtOAc), resulting in the product 13 as a colorless oil (40 mg, 41%): Rf 0.24 (8:1, DCM:EtOAc); [alpha]24D -48.5E (c 1.2, CHCl3); 13C-NMR (500 MHz, CDCl3) delta 148.5, 146.9, 143.3, 134.2, 131.9, 130.1, 129.5, 128.8, 127.6, 123.8, 120.8, 109.6, 108.5, 103.0, 101.3, 58.7, 56.3, 55.8, 28.5; 1H-NMR (300 MHz, CDCl3) delta 1.30 (3H, d, J= 6.9 Hz, CH3), 1.46 (9H, s, Boc), 1.72 (IH, m, Pro), 1.90 (3H, m, Pro), 2.62 (IH, m), 3.23 (IH, m), 3.44 (IH, m), 3.49 (3H, s, OCH3), 3.58 (IH, m), 3.74 (3H, s, OCH3) 3.85 (3H, s, OCH3), 3.90 (IH, m), 5.92 (2H, s, -OCH2-), 6.38 (IH, d, J= 12.3 Hz, vinyl H), 6.45 (IH, s, ArH), 6.46 (IH, d, J = 12.0 Hz, vinyl H), 6.47 (IH, s, ArH), 6.69 (IH, d, J= 8.7, ArH), 6.96 (IH, dd, J= 8.4, 1.8 Hz, ArH), 8.30 (IH, d, J= 2.4, ArH), 8.41 (IH, br); and HRMS calcd for C31H41N2O8 [M+H]+ 569.2863, found 569.2884. Anal, calcd for C31H40N2O8: C, 65.48; H, 7.09; N, 4.93. Found: C, 64.92; H, 7.42; N, 4.97. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diethyl cyanophosphonate; N-ethyl-N,N-diisopropylamine; In dichloromethane; for 16h; | [0481] Cbz-Phe-Tetrazole (2.25 g, 6.25 mmole) was then dissolved in ethanol (100 ml) and treated with Pd/C 10 % (500 mg, 0.3125 mmole) and stirred under hydrogen for 2 hr. The reaction mixture was filtered through a celite pad and concentrated to dryness. This material was reconstituted in dichloromethane (80 ml) and treated with Boc-Dap (1.88 g, 6.54 mmole), DEPC (1.42 ml, 9.38 mmole) and DIEA (3.8 ml, 21.88 mmole). After 16 hr volatiles were removed to afford crude Boc-Dap-Phe-Tetrazole which was purified by preparative HPLC to give 704 mg (20 %) of 1001 as a white powder. Reverse-phase HPLC analysis: 99% at 6.3 min; LCMS(ESI): m/z 458.905 (MH)+, 480.874 (M+Na)+, eluted at 12.95 min. | |
150 mg | With diethyl cyanophosphonate; triethylamine; In dichloromethane; at 0 - 20℃; for 18h; | Compound 80c (210 mg, 1.11 mmol) and KI-2 (351 mg, 1.22 mmol) were dissolved in DCM (20 mL), and the solution was cooled to 0C, to which TEA (336 mg, 3.33 mmol) and DEPC (235 mg, 1.44 mmol) were sequentially added. The reaction mixture was stirred at rt for 18 h, and then concentrated to remove the solvent. The residue was purified by silica gel chromatography (DCM/MeOH 10:1) to give a pale yellow solid 81c (150 mg). LC-MS (Method 1): R = 1.89 mm; m/z (ESj = 459.3 (M+H)t |
Tags: 120205-50-7 synthesis path| 120205-50-7 SDS| 120205-50-7 COA| 120205-50-7 purity| 120205-50-7 application| 120205-50-7 NMR| 120205-50-7 COA| 120205-50-7 structure
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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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