* 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.
Stage #1: With oxalyl dichloride; N,N-dimethyl-formamide In dichloromethane at 0℃; Stage #2: With aluminum (III) chloride In dichloromethane at 0℃; for 1.15 h;
General Procedure D for the Synthesis of Fluoroethyl Substituted Indan Ureas: To a solution of 3-(substituted-phenyl)-propionic acid in CH2Cl2 at 0° C. was added oxalyl chloride (1.5 eq) followed by 2-3 drops of DMF (in case of SOCl2, benzene would be used as solvent, and the reaction mixture would be refluxed for 3 hours). The resulting mixture was stirred until no more gas evolution was observed. After concentration of the reaction mixture, the residue was dissolved in CH2Cl2, cooled to 0° C., and AlCl3 (1.0 eq) was added in 3 batches at 3-minute interval. After stirring for 1 hour, the reaction mixture was quenched in ice-water and the layers were separated. The aqueous layer was extracted with Et2O (3.x.150 mL) and the combined organic extracts were washed with H2O (3.x.100 mL), saturated NaHCO3 (3.x.100 mL), brine (1.x.100 mL), dried over MgSO4 and concentrated. Purification by column chromatography using hexane:EtOAc (4.5:0.5) as eluant gave the desired substituted indanone. The indanone was converted to the desired fluoroethyl ureas via the protocol described in general procedure C. This method may be adapted to other cycloalkyl-aryl fused rings systems using starting materials such as those shown below.Synthesis of 1-(4-chloro-indan-1-yl)-3-(2-fluoro-ethyl)-ureaThe title compound was generated from commercially available 3-(2-chloro-phenyl)-propionic acid according to general procedure D. The intermediates 4-chloro-1-indanone and 4-chloroindan-1-ylamine were isolated and characterized.4-Chloro-1-indanone12: 5.56 g (62percent) of the title indanone was obtained from 3-(2-chloro-phenyl)-propionic acid (10.00 g, 54.20 mmol), oxalyl chloride (32.50 mL, 372.55 mmol) of and AlCl3 (8.00 g, 60.00 mmol) according to general procedure D. Spectroscopic data: 1H NMR (300 MHz, CDCl3) δ 2.70-2.78 (m, 2H), 3.1 (t, 2H, J=5.9 Hz), 7.3 (t, 1H, J=7.6 Hz), 7.58 (d, 1H, J=7.6 Hz), 7.63 (d, 1H, J=7.6 Hz).
Reference：
[1] Synthetic Communications, 2007, vol. 37, # 13, p. 2171 - 2177
[2] Patent: US2008/255239, 2008, A1, . Location in patent: Page/Page column 18; 19
[3] Bulletin de la Societe Chimique de France, 1966, p. 3618 - 3625
[4] Tetrahedron, 1984, vol. 40, # 23, p. 4973 - 4980
[5] Tetrahedron Letters, 2004, vol. 45, # 8, p. 1741 - 1745
[6] Journal of Medicinal Chemistry, 2003, vol. 46, # 3, p. 399 - 408
[7] Patent: US6627764, 2003, B1,
[8] South African Journal of Chemistry, 2010, vol. 63, p. 83 - 87
2
[ 1643-28-3 ]
[ 1866-38-2 ]
[ 15115-59-0 ]
Reference：
[1] Patent: US5177075, 1993, A,
3
[ 1643-28-3 ]
[ 15115-59-0 ]
[ 67120-40-5 ]
Reference：
[1] Patent: US4096173, 1978, A,
4
[ 2033-24-1 ]
[ 89-98-5 ]
[ 1643-28-3 ]
Yield
Reaction Conditions
Operation in experiment
67%
at 10 - 100℃; for 4 h;
General procedure: A three-necked flask fitted with a dropping funnel, reflux condenser and thermometer was charged with 85percent formic acid (8 mL, 180 mmol). After cooling the solution to 5 °C, triethylamine (2.7 mL, 27 mmol) was added dropwise maintaining the temperature below 10 °C. Subsequently, 2-bromobenzaldehyde (7a, 5 g, 27 mmol) and Meldrums acid (3.9 g, 27 mmol) were added to the solution and the mixture was refluxed for 4 h. Afterwards the mixture was cooled to an ambient temperature and poured onto ice-cold water (30 mL). The resulting suspension was acidified by 5.5M HCl until pH ≈ 1 and stored in a refrigerator overnight. The precipitated crystals were filtered with suction, washed with water (3 20 mL), dried in desiccator and dissolved in chloroform (100 mL). Undissolved impurities were filtered off. The filtrate was concentrated to the volume of about 10 mL and petroleum ether (15 mL) was added under stirring and heating the solution. After gradual cooling a white solid was formed. Yield 4.17 g (67percent) of solid with mp 93–95 °C (ref. [8] reports 99–100 °C). Proton NMR spectrum is in accordance with ref.[8]
Reference：
[1] Synthetic Communications, 1995, vol. 25, # 19, p. 3067 - 3074
[2] Beilstein Journal of Organic Chemistry, 2015, vol. 11, p. 884 - 892
[3] Journal of Heterocyclic Chemistry, 2018, vol. 55, # 3, p. 670 - 684
5
[ 704-96-1 ]
[ 1643-28-3 ]
Reference：
[1] South African Journal of Chemistry, 2010, vol. 63, p. 83 - 87
[2] Tetrahedron Letters, 2007, vol. 48, # 3, p. 465 - 467
[3] Chemische Berichte, 1956, vol. 89, p. 2799,2806
[4] Journal of the American Chemical Society, 1937, vol. 59, p. 392,396
6
[ 3752-25-8 ]
[ 1643-28-3 ]
Reference：
[1] Chemische Berichte, 1918, vol. 51, p. 582
[2] Monatshefte fuer Chemie, 1913, vol. 34, p. 1669
[3] Monatshefte fuer Chemie, 1913, vol. 34, p. 1660
[4] Chemische Berichte, 1911, vol. 44, p. 644[5] Chemische Berichte, 1909, vol. 42, p. 4866
[6] Chemische Berichte, 1883, vol. 16, p. 2037
[7] Collection of Czechoslovak Chemical Communications, 1967, vol. 32, p. 4082 - 4098
[8] Journal of the Chinese Chemical Society, 2004, vol. 51, # 5 A, p. 917 - 921
[9] Tetrahedron Letters, 2010, vol. 51, # 27, p. 3536 - 3537
[10] Patent: US2008/255230, 2008, A1, . Location in patent: Page/Page column 14; 18
Reference：
[1] Chemical Communications, 2013, vol. 49, # 32, p. 3306 - 3308
16
[ 95-49-8 ]
[ 1643-28-3 ]
Reference：
[1] Journal of the American Chemical Society, 1949, vol. 71, p. 2644,2646
[2] Journal of the American Chemical Society, 1949, vol. 71, p. 2644,2646
17
[ 77738-21-7 ]
[ 1643-28-3 ]
Reference：
[1] Journal of the American Chemical Society, 1949, vol. 71, p. 2644,2646
18
[ 611-17-6 ]
[ 1643-28-3 ]
Reference：
[1] Journal of the American Chemical Society, 1949, vol. 71, p. 2644,2646
19
[ 611-19-8 ]
[ 1643-28-3 ]
Reference：
[1] Journal of the American Chemical Society, 1949, vol. 71, p. 2644,2646
20
[ 501-52-0 ]
[ 1643-28-3 ]
[ 2019-34-3 ]
Reference：
[1] Organic and Biomolecular Chemistry, 2006, vol. 4, # 14, p. 2716 - 2723
[2] Organic and Biomolecular Chemistry, 2006, vol. 4, # 14, p. 2716 - 2723
EXAMPLE 10 Preparation of Fmoc-(D,L)-5-chloro-2 aminotetraline-2-carboxylic acid (Fmoc-(D,L) 5-ClAtc-OH) A mixture of <strong>[1643-28-3]3-(2-chlorophenyl)propanoic acid</strong> (5.0 g, 27.1 mmole), thionyl chloride (10.9 ml, 149 mmole) and toluene (75 ml) was refluxed for two hours. Concentration in vacuo gave 3-(2-chlorophenyl)propanoyl chloride which was taken up in methylene chloride and used in the next step without further purification.
With thionyl chloride; In toluene;
Step 1 A mixture of <strong>[1643-28-3]3-(2-chlorophenyl)propanoic acid</strong> (5.0 g, 27.1 mmole), thionyl chloride (10.9 ml, 149 mmole) and toluene (75 ml) was refluxed for two hours. Concentration in vacuo gave 3-(2-chlorophenyl)propanoyl chloride which was taken up in methylene chloride and used in the next step without further purification.
With thionyl chloride; In dichloromethane; at 20℃; for 3h;Inert atmosphere;
Intermediate 6 3-(2-chlorophenyl)propanamide To a solution of <strong>[1643-28-3]3-(2-chlorophenyl)propanoic acid</strong> (1.0 g, 5.42 mmol) in DCM (100 mL) was added thionyl chloride (0.39 mL, 5.42 mmol) dropwise under nitrogen. The solution was stirred at room temperature for 3 h and then concentrated. The residue was dissolved in anhydrous THF (10 mL) nd cooled to 0C. 7M Ammonia in methanol (1.55 mL) was added dropwise under nitrogen. The reaction was stirred at room temperature for 4 h and then concentrated. The residue was dissolved in EtOAc (50 mL) and washed with saturated NaHC03 (aq) (2 x 25 mL) and brine (25 mL). The organic phase was dried (MgSO_i), filtered and concentrated, to afford the title compound as a yellow solid (530 mg, 53%); m z = 183.9, 185.9 (MH)+.
General Procedure D for the Synthesis of Fluoroethyl Substituted Indan Ureas: To a solution of 3-(substituted-phenyl)-propionic acid in CH2Cl2 at 0 C. was added oxalyl chloride (1.5 eq) followed by 2-3 drops of DMF (in case of SOCl2, benzene would be used as solvent, and the reaction mixture would be refluxed for 3 hours). The resulting mixture was stirred until no more gas evolution was observed. After concentration of the reaction mixture, the residue was dissolved in CH2Cl2, cooled to 0 C., and AlCl3 (1.0 eq) was added in 3 batches at 3-minute interval. After stirring for 1 hour, the reaction mixture was quenched in ice-water and the layers were separated. The aqueous layer was extracted with Et2O (3×150 mL) and the combined organic extracts were washed with H2O (3×100 mL), saturated NaHCO3 (3×100 mL), brine (1×100 mL), dried over MgSO4 and concentrated. Purification by column chromatography using hexane:EtOAc (4.5:0.5) as eluant gave the desired substituted indanone. The indanone was converted to the desired fluoroethyl ureas via the protocol described in general procedure C. This method may be adapted to other cycloalkyl-aryl fused rings systems using starting materials such as those shown below.Synthesis of 1-(4-chloro-indan-1-yl)-3-(2-fluoro-ethyl)-ureaThe title compound was generated from commercially available 3-(2-chloro-phenyl)-propionic acid according to general procedure D. The intermediates 4-chloro-1-indanone and 4-chloroindan-1-ylamine were isolated and characterized.4-Chloro-1-indanone12: 5.56 g (62%) of the title indanone was obtained from 3-(2-chloro-phenyl)-propionic acid (10.00 g, 54.20 mmol), oxalyl chloride (32.50 mL, 372.55 mmol) of and AlCl3 (8.00 g, 60.00 mmol) according to general procedure D. Spectroscopic data: 1H NMR (300 MHz, CDCl3) delta 2.70-2.78 (m, 2H), 3.1 (t, 2H, J=5.9 Hz), 7.3 (t, 1H, J=7.6 Hz), 7.58 (d, 1H, J=7.6 Hz), 7.63 (d, 1H, J=7.6 Hz).
With aluminium trichloride; thionyl chloride; In (2S)-N-methyl-1-phenylpropan-2-amine hydrate; n-heptane; dichloromethane; water; toluene;
EXAMPLE 2 Preparation of 4-chloroindanone 33.5 g (181 mmol) of the <strong>[1643-28-3]1-(2-carboxyethyl)-2-chlorobenzene</strong> and 83.4 ml of thionyl chloride are placed in a reaction vessel and stirred at 80 C. for one hour. The excess thionyl chloride is subsequently taken off and the residue is admixed with 200 ml of heptane. The reaction mixture is stirred for 30 minutes and the solvent is subsequently removed in an oil pump vacuum. The residue is taken up in 536 ml of methylene chloride and, while cooling in ice, 48.4 g (363 mmol) of aluminum trichloride are added a little at a time over a period of 10 minutes. The resulting reaction solution is stirred at 0 C. for another 2 hours before the reaction mixture is poured onto 300 ml of ice water. After the aqueous phase has been separated off and extracted once with 60 ml of toluene, the combined organic phases are washed with 80 ml of water and with 100 ml of saturated NaCl solution. After drying over magnesium sulfate, the solvent is removed in an oil pump vacuum. 29 g (96%) of the desired product are isolated.
2-Methyl-propane-2-sulfinic acid [(S)-1-(2-{4-[3-(2-chloro-phenyl)-propionyl]-piperazin-1-yl}-5-trifluoromethyl-phenyl)-3-methyl-butyl]-amide[ No CAS ]
With hydrogenchloride; potassium hydroxide; sodium ethanolate; In ethanol; n-heptane; water;
EXAMPLE 1 Preparation of 1-(2-carboxyethyl)-2-chlorobenzene A solution of 171.0 g (2.51 mol) of sodium ethoxide in ethanol is admixed with 149.2 g (932 mmol) of diethyl malonate. 50.0 g (311 mmol) of 2-chlorobenzyl chloride are added to this reaction mixture, and after the addition is complete the reaction mixture is refluxed for three hours. After cooling to room temperature, 480 g (1.71 mol) of a KOH solution are added and the mixture is subsequently refluxed for another hour. The ethanol is then distilled off and the residue is subjected to an aqueous work-up and extracted three times with 100 ml each time of diethyl ether. The organic phase is discarded and the aqueous phase is brought to a pH of 1 using concentrated HCl. The mixture is subsequently extracted three times with 100 ml each time of diethyl ether. The combined organic phases are washed with 100 ml of water and then with 100 ml of a saturated NaCl solution. After drying over magnesium sulfate, the solvent is removed in an oil pump vacuum. The residue is taken up in heptane and subsequently heated to 180 C. After gas evolution has ceased, the solvent is removed in an oil pump vacuum. 43.8 g (91%) of the desired product are isolated. The product prepared is used without further purification for the next step.
Conventional work-up gave 3-(2-chlorophenyl)propanoic acid (26.3 g) which was added to polyphosphoric acid (220 g) at 80 under nitrogen. After stirring for 2 hours at 80 the mixture was allowed to cool and added to water, ether extraction and conventional work up gave 4-chloroindan-1-one as a brown solid (10 g).
55
[ 1643-28-3 ]
[ 1866-38-2 ]
[ 15115-59-0 ]
Yield
Reaction Conditions
Operation in experiment
With PPA;Ra/Ni; In tetrahydrofuran; water;
3-(2-Chlorophenyl)-propanoic acid A solution of 25.0 g of 3'-chlorocinnamic acid (137 mmol) was hydrogenated in 200 ml of THF with 2 g of Ra/Ni at three atmospheres for 16 hours. Then an additional 1.5 g of Ra/Ni was added and the reaction continued for an additional two hours. The solution was filtered and concentrated to give 23.2 g (92%) of material suitable for the next step. A 3.0-g sample was recrystallized from toluene to give 1.6 g of analytical material (53% recovery); mp 97-99. A mixture of 200 ml of polyphosphoric acid and 23.6 g (128 mmol) of 3-(2-chlorophenyl)-propanoic acid was heated on the steam bath for six hours. The mixture was allowed to cool, diluted with 500 ml of water, and the resulting solid collected. The solid was partitioned between ether and saturated sodium bicarbonate, the ether layer was separated, dried (MgSO4), and concentrated to a solid. The solid was crystallized from ether/hexane to give 7.8 g (37%) of 4-chloro-2,3-dihydro-1H-inden-1-one; mp 89-92.
Methyl 3-(2-chlorophenyl)propionate was refluxed in 10% aqueous sodium hydroxide (1 l.) for two hours and the reaction mixture was cooled, acidified and filtered. The filter cake was dissolved in hot aqueous sodium bicarbonate and filtered. The filtrate was acidified and filtered to yield 3-(2-chlorophenyl)propionic acid.
EXAMPLE 1 Preparation of 4-Chloro-1-Aminoindane Following the procedure of J. Am. Chem. Soc., 59, 394 (1937) and Coll. Czech. Chem., 27, 2413 (1962), 55.4 g. of beta-(o-chlorophenyl)propionic acid and about 550 g. of polyphosphoric acid were heated to 100 C. with stirring for one hour. The hot reaction mixture was poured into 2.5 l. of an ice-water mixture. The resulting aqueous layer was extracted twice with chloroform. The chloroform extracts were combined and washed, first with water and then with 2N aqueous sodium hydroxide solution followed by a wash with a saturated aqueous sodium chloride solution. The chloroform layer was separated, dried and decolorized. Evaporation of the chloroform yielded a tan solid comprising 4-chloro-1-indanone formed in the above reaction. The compound, after being recrystallized from a benzene-hexane solvent mixture, melted at 86-90 C.; yield = 16.8 g. Analysis Calc.: C, 64.88; H, 4.24; Cl, 21.28; Found: C, 65.13; H, 4.01; Cl, 21.59.
Example 23; JV-{4-(3-chlorophenyl)-5-i(2-chlorophenyl)met yl]-l,3-thiazol-2-yI}-2-[4- (ethylsuIfonyl)phenyl]acetamide; Intermediate 23a: 5-(2-cMorobenzyl)-4-(3-chlorophenyl)thiazol-2-amine; Step 1:; Borane-tetrahydrofuran complex (17.67 mL) was added dropwise to a solution of 3-(2- chlorophenyl)propanoic acid (1.3 g) in THF (50 mL) cooled at 0 C over 30 mins. The reaction mixture was warmed to room temperature and stirred overnight, The mixture was then cooled to 0 C and quenched with brine. The organic layer was separated, and the aqueous layer was extracted with etiryl acetate (100 mL x 2). The combined organic phases were dried over sodium sulfate and concentrated to afford 3-(2-chlorophenyl)propan-l-ol (1.7 g) as a yellow oil. MSfES^ m/z 153 ((MH- H20)+).
With lithium aluminium tetrahydride; In tetrahydrofuran; at 0℃; for 14h;
3-(2-Chloro-phenyl)-acrylic acid (10.00 g, 55.00 mmol) in THF was mixed with Rh/Al2O3 (800 mg) and hydrogenated at 50 psi for 6 hours. The resulting mixture was filtered through a pad of celite and the filtrate was concentrated. The residue was dissolved in THF and cooled to 0 C. LAH (55.00 mL, 1.0 M in THF, 55.00 mmol) was added and the reaction mixture was stirred for 14 hours. The resulting mixture was quenched with NaOH and extracted with Et2O (3×250 mL). The combined organic extracts were washed with H2O (3×150 mL), brine (1×150 mL), dried over MgSO4 and concentrated to give the title alcohol.
4-(5-amino-6-chloro-2-quinolinyl)-1-piperazinecarboxylic acid 1,1-dimethylethyl ester[ No CAS ]
[ 1643-28-3 ]
2-chloro-N-[6-chloro-2-(1-piperazinyl)-5-quinolinyl]-benzenepropanamidedi hydrochloride[ No CAS ]
Yield
Reaction Conditions
Operation in experiment
(b) 2-CHLORO-N- [6-CHLORO-2- (L-PIPERAZINYL)-5-QUINOLINYL]-BENZENEPROPANAMIDE, dihydrochloride To a stirred solution of 2-chloro-benzenepropanoic acid (204 mg) in dichloromethane (2 mL) at 0C under nitrogen, was added N, N-dimethylformamide (1 drop) and oxalyl chloride (0.3 mL). The reaction mixture was heated to reflux for 2 hours, then cooled, evaporated to dryness and redissolved in dichloromethane (1 ML). This solution was added to a stirred solution OF 4- (5-AMINO-6-CHLORO-2-QUINOLINYL)-PIPERAZINECARBOXYLIC acid, 1,1- dimethylethyl ester (Example 10 (a) ) (200 mg) and potassium carbonate (380 mg) in acetone (2 ML). The reaction mixture was stirred at room temperature for 16 hours then the acetone was evaporated. The residue was redissolved in dichloromethane then poured into water and extracted with dichloromethane (3X20 mL). The combined organic extracts were dried, filtered and evaporated. The resulting solid was purified (SI02, methanol: dichloromethane: ammonium hydroxide solution 10: 90: 1 as eluant) then redissolved in methanol and treated with HCl in 1,4-dioxane (4M, 1 mL) for 1 hour. The resultant suspension was evaporated to dryness and recrystallised from methanol/ethyl acetate to give the title compound as a solid (90 mg). 'H NMR (400 MHz, D6-DMSO) 8 10.09 (1H, s), 9.40 (2H, s), 7.89 (1H, d), 7.83-7. 69 (2H, m), 7.50-7. 26 (SH, m), 4.04 (4H, s), 3.25 (4H, s), 3.08 (2H, t), 2.83 (2H, t). MS: APCI (+ve) 429 (M+H+). m. p. 265-270C
With aluminum (III) chloride; trichlorophosphate; at 0 - 20℃; for 10h;Inert atmosphere;
Phloroglucinol (1.26 g, 10 mmol, Aldrich), <strong>[1643-28-3]3-(2-chlorophenyl)propionic acid</strong> (1.84 g; 10 mmol; Alfa Aesar), and anhydrous A1C13 (5.00 g; 37.5 mmol; Aldrich) were added to a flame-dried 100 ml round-bottom flask. POCl3 (25.15 g; 15 ml; 164 mmol, Aldrich) was added at 0C. The reaction mixture was stirred under N2 for 2 h at 0C and 8 h at room temperature and then was poured into crushed ice (100 g) and extracted with ethyl acetate (3x100 ml). The organic layer was dried over anhydrous Na2S04 and evaporated under vacuum to yield an oily residue. Product 1 was isolated by chromatography on silica gel. Yield: 40%. MS (MALDI): calculated, m/z 293.1 (MH* ; found, 293.1.
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃; for 16h;Inert atmosphere;
General procedure: Mixtures of 4-(di-tert-butoxycarbonylamino)-6-amino-2-methylquinoline (100mg, 0.27mmol), the respective carboxylic acid (0.53mmol, 2equiv), 2-(7-aza-1H-benzotriazole-1-yl)-1,1,3,3-tetramethyluronium hexafluorophosphate (HATU; 190mg, 0.500mmol, 2.0equiv) and di-iso-propylethylamine (0.5mL, 2.9mmol, 10equiv) in DMF (5mL) were stirred at room temperature for 16h. The mixtures were poured into 50mL of 5% aq Na2CO3 and extracted with EtOAc (3×50mL). The combined organic layers were washed with 5% aq Na2CO3 (1×50mL), brine (1×50mL), dried (MgSO4), and evaporated. The residual materials were co-evaporated with diethyl ether and treated without further purification with 1:1 TFA/DCM (5mL) for 30min-2h. Removal of solvents gave crude materials as solids or oils that were triturated with diethyl ether and recrystallized from CH3CN/MeOH) to yield the final product as a TFA salt or purified using prep TLC (80:18:2 CHCl3/MeOH/aq CH3NH2) to provide the free base. Some of the free bases were further reacted with a slight excess of p-toluenesulfonic acid in diethyl ether to provide the corresponding p-TsOH salts.
With N-ethyl-N,N-diisopropylamine; N-[(dimethylamino)-3-oxo-1H-1,2,3-triazolo[4,5-b]pyridin-1-yl-methylene]-N-methylmethanaminium hexafluorophosphate; In N,N-dimethyl-formamide; at 20℃;Sealed tube;
In a sealed tube, tert-butyl 4-(4-aminophenyl)-1H-pyrazole-1-carboxylate (120 mg, 463 mumol), <strong>[1643-28-3]3-(2-chlorophenyl)propanoic acid</strong> (85.4 mg, 463 mumol) and DIPEA (102 mg, 137 mul, 787 mumol) were combined with DMF (1 ml). Then HATU (264 mg, 694 mumol) was added. The mixture was stirred overnight at RT, and then poured into 30 ml ethyl acetate and extracted with water (3 x 15 mL) and brine. The organic layers were dried over sodium sulfate and concentrated in vacuo. tert-Butyl 4-(4-(3-(2-chlorophenyl)propanamido)phenyl)-1H-pyrazole-1-carboxylate was obtained as a light brown foam (240mg, 97.4 %). MS (m/e) = 326.5.
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