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CAS No. : | 60886-80-8 | MDL No. : | MFCD09992876 |
Formula : | C10H15NO2S | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | - |
M.W : | 213.30 | Pubchem ID : | - |
Synonyms : |
|
Num. heavy atoms : | 14 |
Num. arom. heavy atoms : | 0 |
Fraction Csp3 : | 0.9 |
Num. rotatable bonds : | 0 |
Num. H-bond acceptors : | 3.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 59.3 |
TPSA : | 54.88 Ų |
GI absorption : | High |
BBB permeant : | Yes |
P-gp substrate : | No |
CYP1A2 inhibitor : | No |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.83 cm/s |
Log Po/w (iLOGP) : | 1.66 |
Log Po/w (XLOGP3) : | 1.08 |
Log Po/w (WLOGP) : | 2.3 |
Log Po/w (MLOGP) : | 1.92 |
Log Po/w (SILICOS-IT) : | 2.3 |
Consensus Log Po/w : | 1.85 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -1.84 |
Solubility : | 3.06 mg/ml ; 0.0144 mol/l |
Class : | Very soluble |
Log S (Ali) : | -1.82 |
Solubility : | 3.2 mg/ml ; 0.015 mol/l |
Class : | Very soluble |
Log S (SILICOS-IT) : | -2.58 |
Solubility : | 0.564 mg/ml ; 0.00264 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 0.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 5.11 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | 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 |
---|---|---|
84% | With thionyl chloride In chloroform at 60℃; for 3 h; | General procedure: A mixture of sulfonamide 1 (2.0 mmol, 1.0 equiv.), formamide2 (2.0 mmol, 1.0 equiv.) and thionyl chloride (0.236 g, 145 µL,2.0 mmol) in CHCl3 (2.0 mL) was stirred at 60°C for the indicated reaction time (see Table 2). Then, the solvent was evaporated under vacuum to give the products in excellent yields orthe residue was purifed by silica gel column chromatography(petroleum ether and ethyl acetate) to give the desired products. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
28.7% | Stage #1: With potassium hydroxide; dihydrogen peroxide In n-heptane; diethylene glycol dimethyl ether; water at 17℃; for 11 h; Stage #2: With hydrogenchloride; sodium sulfite In diethylene glycol dimethyl ether; water at 5 - 21℃; for 1.58333 h; |
In a round-bottomed flask, 40.00 g (0.105 mol) of (3aS,6R,7aR)-1-[(2S)-2-allyloctanoyl]-8,8-dimethylhexahydro-3a,6-methano-2,1-benzoisothiazole 2,2-dioxide and 160 ml of diglyme were placed, and the mixture was cooled to 17° C. while nitrogen was being sent thereto with the intention of limiting the concentration of oxygen to 5percent or less until the end of the reaction. After 0.51 g (0.005 mol) of 35percent hydrogen peroxide solution was inpoured, 15.79 g (0.162 mol) of 35percent aqueous hydrogen peroxide solution and 19.61 g (0.168 mol) of 48percent aqueous potassium hydroxide solution were simultaneously inpoured at 17° C. over 9 hours, followed by stirring at 17° C. for 2 hours, and the end of the reaction was checked by HPLC.Separately, 21.14 g (0.168 mol) of sodium sulfite was dissolved in 110 ml of water in a flask with a stop-cock at room temperature, 58.97 g (0.566 mol) of 35percent hydrochloric acid was added dropwise at 9 to 10° C., and then the above-mentioned reaction mixture was added dropwise thereto at 5 to 12° C. over 1 hour. After the resultant mixture was heated to 21° C. and stirred at the same temperature for 35 min, 200 ml of methyl tert-butyl ether was inpoured thereto, the mixture was stirred for 10 min, and the water layer was removed by separation. The organic layer was washed with saline solution (1.60 g NaCl, 200 ml tap water), 2.40 g of n-heptane and saline solution (1.60 g NaCl, 200 ml tap water) were added thereto, the mixture was stirred for 15 min, the water layer was removed by separation, and the end of washing was checked by GC. The organic layer was concentrated at normal pressures, and 240 ml of n-heptane was added to the obtained residue, which was then vacuum-concentrated until the residue was reduced to about 160 ml. Then, the residue was cooled and stirred at 0 to 10° C. for 30 minutes. The obtained crystal was filtered, washed with 40 ml of n-heptane, and dried under reduced pressure. Thus, 6.48 g of camphorsultam (yield based on (3aS,6R,7aR)-1-[(2S)-2-allyloctanoyl]-8,8-dimethylhexahydro-3a,6-methano-2,1-benzoisothiazole 2,2-dioxide: 28.7percent; GC area percentage value: 98.23percent) was obtained. (1S)-2,10-camphorsulfonimine (imine form) was contained in the recovered camphorsultam and couldn't be removed by purification.Meanwhile, the filtrate was concentrated under reduced pressure and n-heptane was added thereto, to obtain 72.17 g (corresponding to 0.105 mol) of (2S)-2-(2-propenyl) octanoic acid/heptane solution. From this of which amount was corresponding to 0.087 mol, cyclohexylamine salt of (2S)-2-(2-propenyl) octanoic acid was derived.In a round-bottomed flask, 241 ml of ethyl acetate, 7.78 g (0.078 mol) of cyclohexylamine were placed and 9.00 g (0.013 mol) of (2S)-2-(2-propenyl) octanoic acid/heptane solution was added dropwise thereto at 20° C. over a 30 minute period, followed by stirring at 20 to 21° C. for 1 hour. Further, 51.00 g (corresponding to 0.074 mol) of (2S)-2-(2-propenyl) octanoic acid/heptane solution was added dropwise thereto at 20° C. over 2 hour 30 min. Then, the mixture was cooled and kept within the range of -3 to 3° C. for 1 hour. The crystal was collected by filtration, washed with 64 ml of cooled ethyl acetate, and dried under reduced pressure. Thus, 20.29 g of cyclohexylamine salt of (2S)-2-(2-propenyl) octanoic acid (yield based on (3aS,6R,7aR)-1-[(2S)-2-allyloctanoyl]-8,8-dimethylhexahydro-3a,6-methano-2,1-benzoisothiazole 2,2-dioxide: 82.1percent; optical purity: 100percent) was obtained. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
88% | Stage #1: With strontium hydroxide In n-heptane; water; isopropyl alcohol at 82℃; for 4 h; Stage #2: With hydrogenchloride In tert-butyl methyl ether; water; isopropyl alcohol |
In a round-bottomed flask, 40.00 g (0.104 mol) of (3aS,6R,7aR)-1-[(2S)-2-allyloctanoyl]-8,8-dimethylhexahydro-3a,6-methano-2,1-benzoisothiazole 2,2-dioxide, 200 ml of isopropanol, 76 ml of water and 15.53 g (0.210 mol) of calcium hydroxide were placed. The mixture was heated to the reflux temperature (about 82° C.), and was maintained at the same temperature for 16 hours. The reaction mixture was added dropwise into a liquid mixture of 80 ml of water and 54.60 g (0.524 mol) of 35percent hydrochloric acid at 10 to 24° C., and then 200 ml of methyl tert-butyl ether was inpoured thereto. After the mixture was stirred for 10 min, the water layer was removed by separation, and then the organic layer was washed twice with 200 ml of water. After the organic layer of which amount was corresponding to 0.103 mol was vacuum-concentrated, an operation cycle of adding 135 ml of n-heptane to the residue and vacuum concentration was repeated three times. Next, 135 ml of n-heptane was added to the concentrate, and then the crystal was filtered. The obtained crystal was washed with 39.7 ml of n-heptane, and then dried under reduced pressure. Thus, 21.34 g of (1S)-(-)-2,10-camphorsultam (95.0percent based on (3aS,6R,7aR)-1-[(2S)-2-allyloctanoyl]-8,8-dimethylhexahydro-3a,6-methano-2,1-benzoisothiazole 2,2-dioxide; GC area percentage value: 99.47percent) was recovered.Meanwhile, the filtrate was concentrated, and n-heptane was added thereto, to obtain 71.69 g (corresponding to 0.103 mol) of (2S)-2-(2-propenyl) octanoic acid heptane solution. From this of which amount was corresponding to 0.099 mol, cyclohexylamine salt of (2S)-2-(2-propenyl) octanoic acid was derived.To be more specific, 273 ml of ethyl acetate and 8.81 g (0.089 mol) of cyclohexylamine were placed in a round-bottomed flask, and 10.19 g (corresponding to 0.015 mol) of the above-obtained (2S)-2-(2-propenyl) octanoic acid/heptane solution was added dropwise thereto at 20° C. over a 30 minute period, followed by stirring at 20 to 21° C. for 1 hour. Further, 57.76 g (corresponding to 0.084 mol) of (2S)-2-(2-propenyl) octanoic acid/heptane solution was added dropwise thereto at 20 to 21° C. over 2 hours and 30 min. Then, the resultant mixture was cooled and kept within the range of -3 to 3° C. for 1 hour. The precipitated crystal was collected by filtration, washed with 73 ml of cooled ethyl acetate, and dried under reduced pressure. Thus, 23.03 g of cyclohexylamine salt of (2S)-2-(2-propenyl) octanoic acid (yield based on (3aS,6R,7aR)-1-[(2S)-2-allyloctanoyl]-8,8-dimethylhexahydro-3a,6-methano-2,1-benzoisothiazole 2,2-dioxide: 82.3percent; optical purity: 100percent) was obtained. |
82.3% | Stage #1: With barium dihydroxide In n-heptane; water; <i>tert</i>-butyl alcohol at 50℃; for 4 h; Stage #2: With hydrogenchloride In tert-butyl methyl ether; water; isopropyl alcohol |
According to the same manner as in Example 1 or 2, hydrolysis was performed using 100 parts of (3aS,6R,7aR)-1-[(2S)-2-allyloctanoyl]-8,8-dimethylhexahydro-3a,6-methano-2,1-benzoisothiazole 2,2-dioxide, under the conditions shown in the following Table 1. The amount of (2S)-2-(2-propenyl) octanoic acid produced in the reaction solution was measured by LC, and the production rate thereof was calculated. The results are shown in the following Table 1. TABLE 1 Solvent Water Base Example Part by Part by Part by Reaction Reaction Production No. Type volume volume Type mol Temperature Time Rate (percent) 3 IPA 500 194Ba(OH)2 2.0 82° C. 1 h 86.1 (Reflux) 4 IPA 500 194Ba(OH)2 2.0 60° C. 1 h 87.5 5 t-BuOH 500 194Ba(OH)2 2.0 50° C. 4 h 82.3 6 IPA 500 194Sr(OH)2 2.0 82° C. 4 h 88.0 (Reflux) The IPA and t-BuOH in the table represent isopropanol and tertiary butanol respectively. (2S)-2-(2-propenyl) octanoic acid produced in Examples 3 to 6 was derived to cyclohexylamine salt. The optical purity measured was 100percent in each Example. |
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