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CAS No. : | 13379-98-1 | MDL No. : | MFCD00458992 |
Formula : | C10H15NO3S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | OXBINBPGHTWHKS-UHFFFAOYSA-N |
M.W : | 229.30 | Pubchem ID : | 2180655 |
Synonyms : |
|
Num. heavy atoms : | 15 |
Num. arom. heavy atoms : | 6 |
Fraction Csp3 : | 0.4 |
Num. rotatable bonds : | 5 |
Num. H-bond acceptors : | 4.0 |
Num. H-bond donors : | 2.0 |
Molar Refractivity : | 58.08 |
TPSA : | 74.78 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) : | -7.05 cm/s |
Log Po/w (iLOGP) : | 1.7 |
Log Po/w (XLOGP3) : | 0.92 |
Log Po/w (WLOGP) : | 1.74 |
Log Po/w (MLOGP) : | 0.74 |
Log Po/w (SILICOS-IT) : | 0.92 |
Consensus Log Po/w : | 1.2 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.81 |
Solubility : | 3.57 mg/ml ; 0.0156 mol/l |
Class : | Very soluble |
Log S (Ali) : | -2.08 |
Solubility : | 1.92 mg/ml ; 0.00839 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.41 |
Solubility : | 0.0896 mg/ml ; 0.000391 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 2.14 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P280-P301+P312-P302+P352-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H302-H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
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* 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 |
---|---|---|
29% | ||
With hydrogen bromide In acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triethylamine In dichloromethane at 20℃; for 1h; Inert atmosphere; | |
99% | With triethylamine In dichloromethane at 0℃; for 17h; | |
99% | With triethylamine In chloroform at 0 - 20℃; for 18h; Inert atmosphere; |
99% | With triethylamine In chloroform at 0 - 20℃; for 18h; Inert atmosphere; | 1 N-(3-Hydroxypropyl)-4-methylbenzenesulfonamide (I) [00029] To a cooled (0 °C) mixture of 3-aminopropan-1-ol (1.9 mL, 24.8 mmol) and Et3N (6.9 mL, 49.6 mmol, 2.0 equiv) in chloroform (4.0 mL) was added a solution ofptoluenesulfonyl chloride (5.21 g, 14.38 mmol, 1.1 equiv) in chloroform (6.0 mL, 2.5 M overall). The mixture was allowed to slowly warm to ambient temperature and stir under inert atmosphere for 18 h. The reaction was then quenched with 5% NaHCO3, and the mixture was extracted with EtOAc (x3). The combined organic layers were washed successively with 5% citric acid, water, 5% NaHCO3, and brine. Then the organic layers were dried over Mg504, filtered, and concentrated in vacuo to provide N-(3-hydroxypropyl)-4-methylbenzenesulfonamide (5.70 g, 24.8 mmol, 99% yield). Carried on to next step without further purification.[00030] Analytical data for I: ‘HNMR (400 MFIz, CDC13) 7.76 (d, J 8.3 Hz, 2H), 7.35-7.29 (m, 2H), 5.62 (t, J 6.1 Hz, 1H), 3.70 (t, J= 5.8 Hz, 2H), 3.07 (q, J= 6.3 Hz, 2H),2.74 (s, 1H), 2.43 (s, 3H), 1.71 (ap p, J= 6.0 Hz, 2H). ‘HNMR data for this product corresponds with literature values. |
91% | With triethylamine In chloroform at 0 - 20℃; for 19h; | |
90% | With triethylamine In dichloromethane at 0℃; for 5h; | |
90% | With triethylamine at 20℃; | |
88% | With triethylamine In dichloromethane | |
84% | With anhydrous sodium carbonate In water monomer for 6.5h; | |
80% | With triethylamine In dichloromethane at 0 - 20℃; | |
80% | With triethylamine In dichloromethane at 0 - 20℃; | |
79% | With triethylamine In dichloromethane at 0℃; for 0.25h; | |
78% | ||
68% | With triethylamine In dichloromethane at 0 - 25℃; for 1h; | |
68% | With triethylamine In dichloromethane at 0℃; for 0.5h; | |
68% | With triethylamine In dichloromethane at 0℃; for 0.5h; | |
With potassium carbonate In N,N-dimethyl-formamide at 125℃; | ||
With triethylamine In tetrahydrofuran; water monomer at 0 - 20℃; | ||
With triethylamine In dichloromethane at 20℃; for 16h; | ||
With triethylamine In dichloromethane at 5℃; for 24h; | ||
With triethylamine In dichloromethane at 0 - 20℃; for 13h; | ||
With triethylamine In chloroform at 0 - 20℃; | ||
In ethyl acetate at 20℃; for 2h; | Typical procedure for the synthesis of starting materials General procedure: Tosylation: To a solution of p-toluenesulfonyl chloride (5 mmol, 1.0 equiv) in EtOAc (10 mL) was added proper alkanolamine (10 mmol, 2.0 equiv). The reaction mixture was stirred for 2 hours at room temperature. After completion of the reaction, the mixture was filtered through silica and washed with EtOAc. The residue was concentrated to give products, which were used to next step without further purification. | |
With triethylamine at 0 - 20℃; for 24h; | ||
With triethylamine In dichloromethane at 0 - 20℃; for 10h; | ||
With triethylamine In dichloromethane at 0 - 20℃; Inert atmosphere; | ||
With pyridine In dichloromethane at 0 - 20℃; for 1h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
95% | With toluene-4-sulfonic acid In diethyl ether for 3h; | |
Yield given; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With pyridine In dichloromethane at 0℃; for 0.333333h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
79% | With sodium periodate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium bromide In dichloromethane; water at 35℃; Inert atmosphere; | |
79% | With sodium periodate; 2,2,6,6-Tetramethyl-1-piperidinyloxy free radical; sodium bromide In dichloromethane; water at 35℃; for 18h; Inert atmosphere; | 2 4-Methyl-N-(3-oxopropyl)benzenesulfonamide (II) [00031] To a mixture of N-(3 -hydroxypropyl)-4-methylbenzenesulfonamide (1.15 g, 5.00 mmol), TEMPO (0.078 g, 0.50 mmol, 0.10 equiv), NaTO4 (1.77 g, 8.25 mmol, 1.65 equiv) and NaBr (0.085 g, 0.825 mmol, 0.165 equiv) was added CH2C12/H20 (45:55, 20.0 mL, 0.25 M). The resulting biphasic mixture was heated to 35 °C. Upon completion of the reaction (18 h; monitored by TLC), the organic layer was separated, and the aqueous layer was extracted with CH2C12. The combined organic layers were concentrated in vacuo, and the residue was partitioned between EtOAc and sat. aq. Na2 S203. The organic layer was then washed successively with H20 and brine, dried over MgSO4, filtered, and concentrated in vacuo. Purification by column chromatography (40:60 to 50:50 EtOAc/hexanes) provided 4-methyl-N- (3-oxopropyl)benzenesulfonamide (0.903 g, 3.97 mmol, 79% yield) as a yellow oil.[00032] Analytical data for II: ‘HNMR (500 IVIFIz, CDC13) 9.73 (s, 1H), 7.74 (d, J 8.3 Hz, 2H), 7.32 (d, J= 8.0 Hz, 2H), 4.92 (t, J= 6.6 Hz, 1H), 3.21 (q, J 6.1 Hz, 2H), 2.75 (t, J = 5.8 Hz, 2H), 2.43 (s, 3H). ‘H NMR data for this product corresponds with literature values. |
78% | With Dess-Martin periodane In dichloromethane for 5h; |
66% | With Dess-Martin periodane In dichloromethane at 0 - 20℃; for 16h; Inert atmosphere; | |
65% | With oxalyl dichloride; dimethyl sulfoxide; diisopropylamine In dichloromethane at -78 - 0℃; for 1.33333h; | |
With oxalyl dichloride; dimethyl sulfoxide; N-ethyl-N,N-diisopropylamine In dichloromethane at -78℃; for 1.33333h; | ||
With pyridinium chlorochromate In dichloromethane at 0℃; for 2h; Molecular sieve; | ||
2.15 g | With oxalyl dichloride; dimethyl sulfoxide; triethylamine In dichloromethane at -78 - 20℃; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With triethylamine In chloroform at 0℃; for 0.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
62% | With caesium carbonate In N,N-dimethyl-formamide for 1.5h; | |
With caesium carbonate In N,N-dimethyl-formamide at 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | With caesium carbonate In N,N-dimethyl-formamide for 1.5h; | |
With caesium carbonate In N,N-dimethyl-formamide at 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
60% | With caesium carbonate In N,N-dimethyl-formamide for 1.5h; | |
With caesium carbonate In N,N-dimethyl-formamide at 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | With caesium carbonate In N,N-dimethyl-formamide for 1.5h; | |
With caesium carbonate In N,N-dimethyl-formamide at 25℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With caesium carbonate In acetonitrile at 25℃; for 18h; | |
86% | With caesium carbonate In N,N-dimethyl-formamide for 1.5h; | |
86% | With caesium carbonate In N,N-dimethyl-formamide at 25℃; for 1.5h; |
55% | Stage #1: 3-[N-(4-methylphenylsulfonyl)amino]propan-1-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil for 1h; Stage #2: prenyl bromide In N,N-dimethyl-formamide; mineral oil for 18h; | |
Stage #1: 3-[N-(4-methylphenylsulfonyl)amino]propan-1-ol With sodium hydride In N,N-dimethyl-formamide; mineral oil at 0℃; for 1h; Inert atmosphere; Stage #2: prenyl bromide In N,N-dimethyl-formamide; mineral oil at 20℃; for 8h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
65% | Stage #1: 3-[N-(4-methylphenylsulfonyl)amino]propan-1-ol With sodium hydride In tetrahydrofuran Heating; Stage #2: methylphosphonic acid dichloroanhydride In tetrahydrofuran Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | Stage #1: 3-[N-(4-methylphenylsulfonyl)amino]propan-1-ol With sodium hydride In tetrahydrofuran Heating; Stage #2: P,P-dichlorophenylphosphine oxide In tetrahydrofuran Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
66% | With caesium carbonate In N,N-dimethyl-formamide for 1.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With caesium carbonate In N,N-dimethyl-formamide for 1.5h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
59% | Stage #1: 3-[N-(4-methylphenylsulfonyl)amino]propan-1-ol With sodium hydride In tetrahydrofuran Heating; Stage #2: O-phenyl phosphorodichloridate In tetrahydrofuran Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
63% | With caesium carbonate In N,N-dimethyl-formamide for 40h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
70% | Stage #1: 3-[N-(4-methylphenylsulfonyl)amino]propan-1-ol With sodium hydride In tetrahydrofuran for 1h; Heating; Stage #2: methylphosphonothioic dichloride In tetrahydrofuran for 3h; Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
61% | Stage #1: 3-[N-(4-methylphenylsulfonyl)amino]propan-1-ol With sodium hydride In tetrahydrofuran Heating; Stage #2: phenylthiophosphonic acid dichloride In tetrahydrofuran Heating; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
93% | With 1H-imidazole; dmap In dichloromethane at 0℃; for 2.5h; | |
78% | With 1H-imidazole; dmap In dichloromethane at 0℃; Inert atmosphere; | |
With dmap; triethylamine In dichloromethane at 0 - 20℃; for 16h; |
With 1H-imidazole In dichloromethane at 20℃; for 22h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 63 percent / cesium carbonate / dimethylformamide / 40 h 2: hydrogen; quinoline / palladium on barium sulfate / methanol / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 86 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 67 percent / pyridinium chlorochromate; celite / CH2Cl2 / 0 - 20 °C | ||
Multi-step reaction with 2 steps 1: 93 percent / Cs2CO3 / acetonitrile / 18 h / 25 °C 2: 67 percent / PCC; Celite / CH2Cl2 / 2 h / 25 °C | ||
Multi-step reaction with 2 steps 1: 86 percent / Cs2CO3 / dimethylformamide / 1.5 h / 25 °C 2: 67 percent / PCC; celite / CH2Cl2 / 2 h / 25 °C |
Multi-step reaction with 2 steps 1.1: sodium hydride / mineral oil; N,N-dimethyl-formamide / 1 h 1.2: 18 h 2.1: dimethyl sulfoxide; oxalyl dichloride / dichloromethane / 0.5 h / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 62 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 77 percent / pyridinium chlorochromate; celite / CH2Cl2 / 0 - 20 °C | ||
Multi-step reaction with 2 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: PCC; celite / CH2Cl2 / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 65 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 85 percent / pyridinium chlorochromate; N-methylmorpholine N-oxide; tetrapropylammonium perruthenate / molecular sieves 4 Angstroem / CH2Cl2 / 1.25 h | ||
Multi-step reaction with 2 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: 83 percent / TPAP; NMO; 4 Angstroem molecular sieves / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 60 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 67 percent / pyridinium chlorochromate; celite / CH2Cl2 / 0 - 20 °C | ||
Multi-step reaction with 2 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: PCC; celite / CH2Cl2 / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 62 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 77 percent / pyridinium chlorochromate; celite / CH2Cl2 / 0 - 20 °C 3: hydrochloric acid / CH2Cl2 / 16 h / -78 °C | ||
Multi-step reaction with 3 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: PCC; celite / CH2Cl2 / 25 °C 3: HCl / CH2Cl2; H2O / 16 h / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 65 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 85 percent / pyridinium chlorochromate; N-methylmorpholine N-oxide; tetrapropylammonium perruthenate / molecular sieves 4 Angstroem / CH2Cl2 / 1.25 h 3: 53 percent / methylaluminum dichloride / CHCl3; hexane / 16 h / Heating | ||
Multi-step reaction with 3 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: 83 percent / TPAP; NMO; 4 Angstroem molecular sieves / 25 °C 3: 53 percent / CH3AlCl2 / CHCl3; various solvent(s) / 27 h / 61 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 65 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 85 percent / pyridinium chlorochromate; N-methylmorpholine N-oxide; tetrapropylammonium perruthenate / molecular sieves 4 Angstroem / CH2Cl2 / 1.25 h 3: 22 percent / methylaluminum dichloride / CHCl3; hexane / 16 h / Heating | ||
Multi-step reaction with 3 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: 83 percent / TPAP; NMO; 4 Angstroem molecular sieves / 25 °C 3: 22 percent / CH3AlCl2 / CHCl3; various solvent(s) / 27 h / 61 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 59 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 61 percent / pyridinium chlorochromate; celite / CH2Cl2 / 0 - 20 °C | ||
Multi-step reaction with 2 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: PCC; celite / CH2Cl2 / 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 60 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 67 percent / pyridinium chlorochromate; celite / CH2Cl2 / 0 - 20 °C 3: 74 percent / methylaluminum dichloride / CHCl3; hexane / 16 h / Heating | ||
Multi-step reaction with 3 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: PCC; celite / CH2Cl2 / 25 °C 3: 74 percent / CH3AlCl2 / CHCl3; various solvent(s) / 27 h / 61 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 60 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 67 percent / pyridinium chlorochromate; celite / CH2Cl2 / 0 - 20 °C 3: 4 percent / methylaluminum dichloride / CHCl3; hexane / 16 h / Heating | ||
Multi-step reaction with 3 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: PCC; celite / CH2Cl2 / 25 °C 3: 4 percent / CH3AlCl2 / CHCl3; various solvent(s) / 27 h / 61 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 59 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 61 percent / pyridinium chlorochromate; celite / CH2Cl2 / 0 - 20 °C 3: 61 percent / methylaluminum dichloride / CHCl3; hexane / 16 h / Heating | ||
Multi-step reaction with 3 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: PCC; celite / CH2Cl2 / 25 °C 3: 61 percent / CH3AlCl2 / CHCl3; various solvent(s) / 27 h / 61 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 59 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 61 percent / pyridinium chlorochromate; celite / CH2Cl2 / 0 - 20 °C 3: 20 percent / methylaluminum dichloride / CHCl3; hexane / 16 h / Heating | ||
Multi-step reaction with 3 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: PCC; celite / CH2Cl2 / 25 °C 3: 20 percent / CH3AlCl2 / CHCl3; various solvent(s) / 27 h / 61 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 63 percent / cesium carbonate / dimethylformamide / 40 h 2: hydrogen; quinoline / palladium on barium sulfate / methanol / 2 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 62 percent / cesium carbonate / dimethylformamide / 1.5 h 2: 77 percent / pyridinium chlorochromate; celite / CH2Cl2 / 0 - 20 °C 3: hydrochloric acid / CH2Cl2 / 16 h / -78 °C | ||
Multi-step reaction with 3 steps 1: Cs2CO3 / dimethylformamide / 25 °C 2: PCC; celite / CH2Cl2 / 25 °C 3: HCl / CH2Cl2; H2O / 16 h / -78 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 100 percent / Et3N / CHCl3 / 0.5 h / 0 °C 2: 82 percent / Et3N / acetonitrile / 4 h / Heating 3: 90 percent / Cu(Ac)2 / 24 h / 20 °C 4: 90 percent / Et3N / CHCl3 / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 100 percent / Et3N / CHCl3 / 0.5 h / 0 °C 2: 82 percent / Et3N / acetonitrile / 4 h / Heating 3: 90 percent / Cu(Ac)2 / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 100 percent / Et3N / CHCl3 / 0.5 h / 0 °C 2: 82 percent / Et3N / acetonitrile / 4 h / Heating 3: 90 percent / Cu(Ac)2 / 24 h / 20 °C 4: 90 percent / Et3N / CHCl3 / 0.5 h / 0 °C 5: 83 percent / Cs2CO3 / dimethylformamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 100 percent / Et3N / CHCl3 / 0.5 h / 0 °C 2: 79 percent / Et3N / acetonitrile / 4 h / Heating 3: 87 percent / Cu(Ac)2 / 24 h / 20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 100 percent / Et3N / CHCl3 / 0.5 h / 0 °C 2: 79 percent / Et3N / acetonitrile / 4 h / Heating 3: 87 percent / Cu(Ac)2 / 24 h / 20 °C 4: 92 percent / Et3N / CHCl3 / 0.5 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: 100 percent / Et3N / CHCl3 / 0.5 h / 0 °C 2: 79 percent / Et3N / acetonitrile / 4 h / Heating 3: 87 percent / Cu(Ac)2 / 24 h / 20 °C 4: 92 percent / Et3N / CHCl3 / 0.5 h / 0 °C 5: 75 percent / Cs2CO3 / dimethylformamide |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: 95 percent / p-TsOH*H2O / diethyl ether / 3 h 2: 1.) KH; 2.) HCl / 1.) DMF-mineral oil, 2.5 h, 50 deg C; 2.) MeOH, 1.5 h, RT |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: pyridine / CH2Cl2 / 0.33 h / 0 °C 2: 99 percent / diisopropylethylamine / CH2Cl2 / 4 h / Ambient temperature 3: 100 percent / aq. LiOH / methanol / 15 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: pyridine / CH2Cl2 / 0.33 h / 0 °C 2: 99 percent / diisopropylethylamine / CH2Cl2 / 4 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: 95 percent / p-TsOH*H2O / diethyl ether / 3 h 2: 1.) KH; 2.) HCl / 1.) DMF-mineral oil, 2.5 h, 50 deg C; 2.) MeOH, 1.5 h, RT 3: 95 percent / pyridine / CH2Cl2 / 0.25 h / 0 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 7 steps 1: pyridine / CH2Cl2 / 0.33 h / 0 °C 2: 99 percent / diisopropylethylamine / CH2Cl2 / 4 h / Ambient temperature 3: 100 percent / aq. LiOH / methanol / 15 h / Ambient temperature 4: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate / CH2Cl2 / 45 h 5: 82 percent / dimethylformamide / 18 h / -20 °C 6: 80 percent / Et3N / CH2Cl2 / 1 h / -15 - 5 °C 7: 58 percent / K2CO3 / acetonitrile / 24 h / Heating |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 1: pyridine / CH2Cl2 / 0.33 h / 0 °C 2: 99 percent / diisopropylethylamine / CH2Cl2 / 4 h / Ambient temperature 3: 100 percent / aq. LiOH / methanol / 15 h / Ambient temperature 4: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate / CH2Cl2 / 45 h 5: 82 percent / dimethylformamide / 18 h / -20 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: pyridine / CH2Cl2 / 0.33 h / 0 °C 2: 99 percent / diisopropylethylamine / CH2Cl2 / 4 h / Ambient temperature 3: 100 percent / aq. LiOH / methanol / 15 h / Ambient temperature 4: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate / CH2Cl2 / 45 h |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 6 steps 1: pyridine / CH2Cl2 / 0.33 h / 0 °C 2: 99 percent / diisopropylethylamine / CH2Cl2 / 4 h / Ambient temperature 3: 100 percent / aq. LiOH / methanol / 15 h / Ambient temperature 4: 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate / CH2Cl2 / 45 h 5: 82 percent / dimethylformamide / 18 h / -20 °C 6: 80 percent / Et3N / CH2Cl2 / 1 h / -15 - 5 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 1: 95 percent / p-TsOH*H2O / diethyl ether / 3 h 2: 1.) KH; 2.) HCl / 1.) DMF-mineral oil, 2.5 h, 50 deg C; 2.) MeOH, 1.5 h, RT 3: 95 percent / pyridine / CH2Cl2 / 0.25 h / 0 °C 4: 70 percent / diisopropylethylamine / CH2Cl2 / 13 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 5 steps 2: 79 percent / K2CO3 / acetonitrile / 24 h / 80 °C 3: 90 percent / MeOH / pTsOH / 1 h / Ambient temperature 4: 98 percent / Et3N / CH2Cl2 / 2 h / -78 - 25 °C 5: 65 percent / Cs2CO3 / dimethylformamide / 7 h / 80 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 2: 79 percent / K2CO3 / acetonitrile / 24 h / 80 °C 3: 90 percent / MeOH / pTsOH / 1 h / Ambient temperature |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 4 steps 2: 79 percent / K2CO3 / acetonitrile / 24 h / 80 °C 3: 90 percent / MeOH / pTsOH / 1 h / Ambient temperature 4: 98 percent / Et3N / CH2Cl2 / 2 h / -78 - 25 °C |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: aq. NaOH / Heating 2: PBr3 / benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1: HBr / acetic acid |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 3 steps 1: aq. NaOH / Heating 2: PBr3 / benzene |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With camphor-10-sulfonic acid In 1,2-dichloro-ethane at 20 - 70℃; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
94% | With amberlyst-15 In dichloromethane at 20℃; for 2h; Inert atmosphere; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
91% | With amberlyst-15 In dichloromethane at 20℃; for 2h; Inert atmosphere; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
82% | With amberlyst-15 In dichloromethane at 20℃; for 2h; Inert atmosphere; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
100% | With amberlyst-15 In dichloromethane at 20℃; for 2h; Inert atmosphere; Molecular sieve; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | Stage #1: 3-[N-(4-methylphenylsulfonyl)amino]propan-1-ol With caesium carbonate In acetonitrile at 20℃; for 0.5h; Stage #2: (E)-1-chloro-4-acetoxybut-2-ene With tetra-(n-butyl)ammonium iodide In acetonitrile at 0 - 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
80% | Stage #1: 3-[N-(4-methylphenylsulfonyl)amino]propan-1-ol With caesium carbonate In acetonitrile at 20℃; for 0.5h; Stage #2: (E)-1-acetoxy-4-chloro-2-[(triethyl)silyl]but-2-ene With tetra-(n-butyl)ammonium iodide In acetonitrile at 0 - 20℃; for 12h; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
38% | With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 40℃; for 16h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
83% | With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 30℃; for 21h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
71% | With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 40℃; for 6h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
32% | With dichloro bis(acetonitrile) palladium(II) In 1,2-dimethoxyethane at 40℃; for 6h; Inert atmosphere; |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
Multi-step reaction with 2 steps 1.1: 1H-imidazole; dmap / dichloromethane / 0 °C / Inert atmosphere 2.1: sodium hydride / tetrahydrofuran; N,N-dimethyl-formamide / 0 - 20 °C / Inert atmosphere 2.2: 0 - 20 °C / Inert atmosphere |
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