[ CAS No. 5872-08-2 ] {[proInfo.proName]}

Name: 5872-08-2|(7,7-Dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonic acid|99%
Brand: Ambeed
SKU: A730355
Price: 6.0 USD
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Quality Control of [ 5872-08-2 ]

COA NMR CNMR HPLC LC-MS

Related Doc. of [ 5872-08-2 ]

SDS Specification

Alternatived Products of [ 5872-08-2 ]

Product Details of [ 5872-08-2 ]

CAS No. :	5872-08-2	MDL No. :	MFCD00074827
Formula :	C₁₀H₁₆O₄S	Boiling Point :	-
Linear Structure Formula :	-	InChI Key :	MIOPJNTWMNEORI-UHFFFAOYSA-N
M.W :	232.30	Pubchem ID :	18462
Synonyms :

Calculated chemistry of [ 5872-08-2 ]

Physicochemical Properties

Num. heavy atoms :	15
Num. arom. heavy atoms :	0
Fraction Csp3 :	0.9
Num. rotatable bonds :	2
Num. H-bond acceptors :	4.0
Num. H-bond donors :	1.0
Molar Refractivity :	56.17
TPSA :	79.82 Å²

Pharmacokinetics

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) :	-7.33 cm/s

Lipophilicity

Log Po/w (iLOGP) :	0.63
Log Po/w (XLOGP3) :	0.54
Log Po/w (WLOGP) :	2.35
Log Po/w (MLOGP) :	1.06
Log Po/w (SILICOS-IT) :	1.07
Consensus Log Po/w :	1.13

Druglikeness

Lipinski :	0.0
Ghose :	None
Veber :	0.0
Egan :	0.0
Muegge :	0.0
Bioavailability Score :	0.56

Water Solubility

Log S (ESOL) :	-1.49
Solubility :	7.54 mg/ml ; 0.0325 mol/l
Class :	Very soluble
Log S (Ali) :	-1.79
Solubility :	3.79 mg/ml ; 0.0163 mol/l
Class :	Very soluble
Log S (SILICOS-IT) :	-1.99
Solubility :	2.37 mg/ml ; 0.0102 mol/l
Class :	Soluble

Medicinal Chemistry

PAINS :	0.0 alert
Brenk :	1.0 alert
Leadlikeness :	1.0
Synthetic accessibility :	4.69

Safety of [ 5872-08-2 ]

Signal Word:	Danger	Class:	8
Precautionary Statements:	P501-P260-P264-P280-P303+P361+P353-P301+P330+P331-P363-P304+P340+P310-P305+P351+P338+P310-P405	UN#:	3261
Hazard Statements:	H314	Packing Group:	Ⅱ
GHS Pictogram:

Application In Synthesis of [ 5872-08-2 ]

* 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.

Downstream synthetic route of [ 5872-08-2 ]

[ 5872-08-2 ] Synthesis Path-Downstream 1~56

1
[ 357-57-3 ]
[ 5872-08-2 ]
[ 3144-16-9 ]
[ 35963-20-3 ]

Reference： [1]Read; Reid [Journal of the Society of Chemical Industry, 1928, vol. 47, p. 11 T][Chemisches Zentralblatt, 1928, vol. 99, # I, p. 2374] Burgess; Gibson [Journal of the Society of Chemical Industry, 1925, vol. 44, # 497, p. 498 T][Chemisches Zentralblatt, 1926, vol. 97, # I, p. 914]

2
[ 76-22-2 ]
[ 5872-08-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; acetic anhydride

Reference： [1]Bartlett; Knox [Organic Syntheses, 1965, vol. 45, p. 12]

3
[ 5872-08-2 ]
[ 3144-16-9 ]

Yield	Reaction Conditions	Operation in experiment
	With brucine man zerlegt das ausscheideten Brucinsalz der <d-Campher>-β-sulfonsaeure mit Barytwasser;
	With brucine

Reference： [1]Rewald [Chemische Berichte, 1909, vol. 42, p. 3136]
[2]Burgess; Gibson [Journal of the Society of Chemical Industry, 1925, vol. 44, p. 497 T][Chemisches Zentralblatt, 1926, vol. 97, # I, p. 914] Read; Reid [Journal of the Society of Chemical Industry, 1928, vol. 47, p. 11 T][Chemisches Zentralblatt, 1928, vol. 99, # I, p. 2374]
[3]Mueller,D.M. et al. [Journal fur praktische Chemie (Leipzig 1954), 1975, vol. 317, p. 689 - 693]

4
[ 5872-08-2 ]
[ 35963-20-3 ]

Yield	Reaction Conditions	Operation in experiment
	With hydrogenchloride; d-phenylglycine
	With brucine

Reference： [1]Ingersoll [Journal of the American Chemical Society, 1925, vol. 47, p. 1172][Organic Syntheses, 1937, vol. 17, p. 80]
[2]Burgess; Gibson [Journal of the Society of Chemical Industry, 1925, vol. 44, p. 497 T][Chemisches Zentralblatt, 1926, vol. 97, # I, p. 914] Read; Reid [Journal of the Society of Chemical Industry, 1928, vol. 47, p. 11 T][Chemisches Zentralblatt, 1928, vol. 99, # I, p. 2374]
[3]Mueller,D.M. et al. [Journal fur praktische Chemie (Leipzig 1954), 1975, vol. 317, p. 689 - 693]

5
[ 464-49-3 ]
[ 5872-08-2 ]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; acetic anhydride Reychler method;

Reference： [1]Majeed, Nesreen N.; Porte, Andrew L. [Journal of the Chemical Society. Perkin transactions II, 1987, p. 1139 - 1146]

6
[ 5872-08-2 ]
[ 21791-95-7 ]

Yield	Reaction Conditions	Operation in experiment
	With potassium hydroxide

Reference： [1]Majeed, Nesreen N.; Porte, Andrew L. [Journal of the Chemical Society. Perkin transactions II, 1987, p. 1139 - 1146]

7
[ 5872-08-2 ]
1,3,3-Trimethyl-5-nitro-2-{(E)-3-[1,3,3-trimethyl-5-nitro-1,3-dihydro-indol-(2E)-ylidene]-propenyl}-2,3-dihydro-1H-indol-2-ol [ No CAS ]
1,3,3,1',3',3'-Hexamethyl-5,5'-dinitroindocarbocyanine dl-10-camphorsulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
81%	With potassium hydroxide In methanol; water

Reference： [1]Murphy, Sean; Yang, Xiquiang; Schuster, Gary B. [Journal of Organic Chemistry, 1995, vol. 60, # 8, p. 2411 - 2422]

8
[ 5872-08-2 ]
C₁₀H₁₅PS₄ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	With tetraphosphorus decasulfide; tetra(n-butyl)ammonium hydroxide 2.) toluene, reflux, 16h; Yield given. Multistep reaction;

Reference： [1]Echarri, Raouf; Matheu, Ma. Isabel; Claver, Carmen; Castillon, Sergio; Alvarez-Larena, Angel; Piniella, Juan F. [Tetrahedron Letters, 1997, vol. 38, # 36, p. 6457 - 6460]

Yield	Reaction Conditions	Operation in experiment
	Racematspaltung mit D-(bzw. L-) Carnitinnitrilhydroxid;

10
[ 7647-01-0 ]
[ 2935-35-5 ]
[ 5872-08-2 ]
[ 3144-16-9 ]
[ 35963-20-3 ]

Reference： [1]Ingersoll [Journal of the American Chemical Society, 1925, vol. 47, p. 1172][Organic Syntheses, 1937, vol. 17, p. 80]

Yield	Reaction Conditions	Operation in experiment
	With sulfuric acid; acetic anhydride

12
[ 5872-08-2 ]
[ 6994-93-0 ]

Yield	Reaction Conditions	Operation in experiment
85%	With thionyl chloride In N,N-dimethyl-formamide at 0 - 20℃; for 4.5h;
	With trichloroacetonitrile; triphenylphosphine In dichloromethane for 1h; Heating;

Reference： [1]Okolotowicz, Karl J.; Lee, Wei-Jen; Hartman, Rosemarie F.; Kim, Ann Y.; Ottersberg, Steven R.; Robinson Jr., Dale E.; Lefler, Scott R.; Rose, Seth D. [Archiv der Pharmazie, 2001, vol. 334, # 6, p. 194 - 202]
[2]Chantarasriwong, Oraphin; Jang, Doo Ok; Chavasiri, Warinthorn [Tetrahedron Letters, 2006, vol. 47, # 42, p. 7489 - 7492]

13
[ 5872-08-2 ]
N-phenethyl-10-camphorsulfonamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: Cl₃CCN; PPh₃ / CH₂Cl₂ / 1 h / Heating 2: 4-picoline / CH₂Cl₂ / 1 h / 20 °C

Reference： [1]Chantarasriwong, Oraphin; Jang, Doo Ok; Chavasiri, Warinthorn [Tetrahedron Letters, 2006, vol. 47, # 42, p. 7489 - 7492]

14
[ 5872-08-2 ]
(+/-)-6-(camphor-10-sulfonamido)-hexanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: 85 percent / SOCl₂ / dimethylformamide / 4.5 h / 0 - 20 °C 2.1: MgO / H₂O; dioxane / 0.25 h / Heating 2.2: 65 percent / H₂O; dioxane / 16 h

15
[ 5872-08-2 ]
(+/-)-6-(camphorquinone-10-sulfonamido)-hexanoic acid [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1.1: 85 percent / SOCl₂ / dimethylformamide / 4.5 h / 0 - 20 °C 2.1: MgO / H₂O; dioxane / 0.25 h / Heating 2.2: 65 percent / H₂O; dioxane / 16 h 3.1: SeO₂ / H₂O; dioxane / 120 h / Heating

16
[ 5872-08-2 ]
10 bromocamphor [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 3 steps 1: KOH 2: PBr₃ 3: xylene / Heating; Dallacker et al. method

Reference： [1]Majeed, Nesreen N.; Porte, Andrew L. [Journal of the Chemical Society. Perkin transactions II, 1987, p. 1139 - 1146]

17
[ 5872-08-2 ]
(+)-10-bromo-2-chloro-2-nitrosocamphane [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 5 steps 1: KOH 2: PBr₃ 3: xylene / Heating; Dallacker et al. method 4: NH₂OH-HCl 5: Cl₂ gas / diethyl ether / 0 °C / Davidson method

Reference： [1]Majeed, Nesreen N.; Porte, Andrew L. [Journal of the Chemical Society. Perkin transactions II, 1987, p. 1139 - 1146]

18
[ 5872-08-2 ]
10-bromocamphor oxime [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 4 steps 1: KOH 2: PBr₃ 3: xylene / Heating; Dallacker et al. method 4: NH₂OH-HCl

Reference： [1]Majeed, Nesreen N.; Porte, Andrew L. [Journal of the Chemical Society. Perkin transactions II, 1987, p. 1139 - 1146]

19
[ 5872-08-2 ]
((1S,4R)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-methanesulfonyl bromide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1: KOH 2: PBr₃

Reference： [1]Majeed, Nesreen N.; Porte, Andrew L. [Journal of the Chemical Society. Perkin transactions II, 1987, p. 1139 - 1146]

20
[ 433937-93-0 ]
[ 5872-08-2 ]
C₁₀H₁₆O₄S*C₂₂H₂₃ClF₂N₄O₅ [ No CAS ]

Reference： [1]Current Patent Assignee: ASTRAZENECA PLC - WO2003/101957, 2003, A1 Location in patent: Page 45-46

21
[ 66-98-8 ]
[ 5872-08-2 ]
C₃₄H₃₆O₈S₂^(2-)*2Na⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 10-camphorsufonic acid With sodium methylate In methanol; toluene at 25 - 66℃; Stage #2: 4,4'-diformylbiphenyl In methanol; toluene at 66 - 70℃; for 7h;	1 EXAMPLE 1 23.3 g (+-) of camphor-10-sulfonic acid are dissolved in 100 ml of toluene and 5 ml of methanol at 25° C. and are then charged with 11.2 g of sodium methylate and the mixture is heated, with stirring, to 66° C. A circa 50° C. warm solution consisting of 10.5 g of 1,1'-diphenyl-4,4'-bisaldehyde in 145 ml of toluene and 16 ml of methanol is then added to the above mixture over 2 hours at 66 to 70° C. This temperature is maintained for another 5 hours until no further increase of the product is found in a DC. Toluene and methanol are then distilled off as an azeotrope while being charged successively with a total of 115 ml of water. A solution forms at 98° C. which is clarified by filtration using some carbon. At about 50° C., 300 ml of methanol are added dropwise and the mixture is cooled to 10° C., the compound crystallising out as a sodium salt. After 2 hours, the precipitate is subjected to filtration and washed with 100 ml of methanol. Drying yields 16.8 g of crude product of the compound of formula (101). To purify the crude product, it is dissolved in 150 ml of methanol and 200 ml of water at 50° C. and clarified by filtration. For crystallisation, 200 ml of brine 15% and 100 ml of methanol are added and the mixture is cooled to 10° C. After 2 hours, the precipitate is collected by filtration, washed with 20 ml of methanol/water 1:1 and dried. A first fraction is obtained which consists of 5.8 g of the pure compound of formula (101). Additional fractions can be obtained from the filtrate.

Reference： [1]Current Patent Assignee: BASF SE - US6384284, 2002, B1 Location in patent: Page column 7

22
[ 5872-08-2 ]
[ 25435-53-4 ]

Yield	Reaction Conditions	Operation in experiment
90%	With potassium hydroxide at 200 - 220℃; for 0.0833333h;

Reference： [1]Hu, Huayou; Faraldos, Juan A.; Coates, Robert M. [Journal of the American Chemical Society, 2009, vol. 131, # 33, p. 11998 - 12006]

23
[ 5872-08-2 ]
[ 81403-68-1 ]
N₁-(4-amino-6,7-dimethoxyquinazol-2-yl)-N₁-methyl-N₂-(tetrahydrofuro-2-yl)propylenediamine (7,7-dimethyl-2-oxo-bicyclo[2,2,1]hept-1-yl)methanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
84%		In a 3 L jacketed reactor provided with mechanical stirring, 232 g (0.544 moles) of crude <strong>[81403-68-1]alfuzosin hydrochloride</strong>, 500 ml_ of water, 55 ml_ of a 30% aqueous solution of sodium hydroxide and 2320 ml_ of methylene chloride were added. The mass was kept under stirring for at least 30 min and, the stirring being stopped, the phases were separated. The organic phase was reloaded and extracted with 550 ml_ of water, then reloaded again and 137 g (0.590 moles) of camphorsulfonic acid at a temperature of about 20 C were added thereto over about 15 min. A complete dissolution is observed. Distillation of dichloromethane under reduced pressure, until the residue could be stirred, by keeping the jacket temperature about 40 C was then performed. 2300 ml_ of toluene were added to the obtained oily residue and the mass was heated up to distillation temperature (870C). The solvent was then distilled by progressively heating the mass, continuing the distillation until the internal temperature of about 1 10C was reached. The obtained mass was slowly cooled up to 20 C, allowed to stir at 20 C for some hours, then the obtained solid was filtrated by washing the panel with 200 ml_ of toluene, oven-dried under reduced pressure at a temperature of 55 C for about 12 hours yielding 285 g (0.458 moles) of [N1(4-amino-6,7-dimethoxyquinazol-2-yl)-N1-methyl-N2-(tetrahydro-furoyl-2)-propylenediamine](7,7-dimethyl-2-oxo-bicycl[2,2,1]hept-1-yl)-methanesulfonate(alfuzosin camphorsulfonate) as a white crystalline solid. Alfuzosin camphorsulfonate: yield 84%; purity determined by HPLC 99.38%.

Reference： [1]Patent: WO2010/10058,2010,A1 .Location in patent: Page/Page column 15; 16

24
[ 5872-08-2 ]
[ 81403-80-7 ]
N₁-(4-amino-6,7-dimethoxyquinazol-2-yl)-N₁-methyl-N₂-(tetrahydrofuro-2-yl)propylenediamine (7,7-dimethyl-2-oxo-bicyclo[2,2,1]hept-1-yl)methanesulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
88%	In ethyl acetate at 20 - 50℃; Inert atmosphere;	6 In one glass jacketed reactor 30 g (0,076 moles) of alfuzosin base, 150 ml_ of ethyl acetate, 21.2 g (0,091 moles) of (+/-)camphoM 0-sulfonic acid (β) were loaded.The mixture was heated at 50 °C under nitrogen for 2 hours without reaching the complete dissolution and then cooled at 20 °C and kept under stirring overnight. Alfuzosin camphorsulfonate salt was obtained in the form of white crystalline powder and isolated by means of filtration, washed with 30 ml_ of ethyl acetate, vacuum dried at 50 °C overnight, thus obtaining 42 g (0.067 moles) of [N1(4-amino-6,7-dimethoxyquinazol-2-yl)-N1-methyl-N2-(tetrahydro-furoyl-2)-propylenediamine](7,7-dimethyl-2-oxo-bicycl[2,2,1]hept-1-yl)-methanesulfonate (alfuzosin camphorsulfonate). Alfuzosin camphorsulfonate salt: yield 88%; purity determined by HPLC 97%

Reference： [1]Current Patent Assignee: H. LUNDBECK A/S - WO2010/10058, 2010, A1 Location in patent: Page/Page column 15

25
[ 1253568-74-9 ]
[ 5872-08-2 ]
N-(3-(9H-purin-6-yl)pyridin-2-yl)-1H-indazol-4-amine (+/-)-10-camphorsulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
86%	In methanol; dichloromethane at 40℃; for 22h;	18.2 STEP 2. N-(3-(9H-PURTN-6-YL)PYRIDIN-2-YL)-l H-IND AZOL-4-AMINE[00164] A solution of 2-(tetrahydro-2H-pyran-2-yl)-N-(3-(9-(tetrahydro-2H-pyran-2-yl)- 9H-purin-6-yl)pyridin-2-yl)-2H-indazol-4-amine (34.8 mg, 70 μmol) in DCM / MeOH (4 mL; 1 : 1) was treated with (+/-)- 10-camphorsulfonic acid (8 mg, 0.5 equiv.) and the mixture stirred for 16 h. About 50% monodeprotection was observed in a clean reaction. An additional 20 mg of CSA was added (1.7 equiv. total). After 1 h, virtually complete monodeprotection observed and about 10% dideprotection. After 3 h, about 27% conversion to fully deprotected compound was observed in a clean reaction by LCMS. An additional 8 mg CSA was added (2.2 equiv. total) and the temperature of the reaction mixture was increased to 40 0C. After a further 3 h, deprotection was essentially complete by LCMS. The volume of the reaction mixture was reduced by about50% under a stream of N2 in order to rmove DCM, and the solution was triturated with Et2θ resulting in the formation of a precipitate which was collected by filtration washing with Et2O and dried under vacuum to giveN-(3-(9H-purin-6-yl)pyridin-2-yl)-lH- indazol-4-amine (+/-)- 10-camphorsulfonate salt (33.7 mg, 86% yield) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ 13.17 (br. s., 1 H); 9.89 (d, 1 H); 9.33 (s, 1 H); 8.76 (s, 1 H); 8.41 - 8.46 (m, 1 H); 8.31 (s, 1 H); 8.24 (d, 1 H); 7.35 (t, 1 H); 7.21 (d, 1 H); 7.14 (t, 1 H); 2.88 (d, 1 H); 2.63 - 2.73 (m, 1 H); 2.34 - 2.42 (d, 1 H); 2.18 - 2.29 (m, 1 H); 1.90 - 1.97 (m, 1 H); 1.74 - 1.90 (m, 2 H); 1.27 (m, 2 H); 1.05 (s, 3 H); 0.75 (s, 3 H). m/z (ESI, +ve) 329.0 (M+H)+.

Reference： [1]Current Patent Assignee: AMGEN INC - WO2010/126895, 2010, A1 Location in patent: Page/Page column 77

26
[ 1445-45-0 ]
[ 5872-08-2 ]
(+/-)-2-oxo-bornane-10-sulfonic acid methyl ester [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
89%	In dichloromethane at 20℃;	3 (+/-)-IO-Camphorsulphonic acid (0.1 mol) was suspended in 230 ml of methylene chloride. Then trimethyl orthoacetate (0.5 mol) was added dropwise. Reaction was carried out for 30 minutes at room temperature. Then the solvent was removed by evaporation, and the residue was triturated in heptane. Obtained crystals were filtered off and dried. Yield: 89%.
89%	In dichloromethane at 20℃;	3 Example 3 Preparation of methyl (±)-10-camphorsulphonate The title compound was obtained according to J. I. Truillo, A. S. Gopalan; Tetrahedron Letters, Vol. 34, No. 46, pp. 7355-7358, 1993. (±)-10-Camphorsulphonic acid (0.1 mol) was suspended in 230 ml of methylene chloride. Then trimethyl orthoacetate (0.5 mol) was added dropwise. Reaction was carried out for 30 minutes at room temperature. Then the solvent was removed by evaporation, and the residue was triturated in heptane. Obtained crystals were filtered off and dried. Yield: 89%.

Reference： [1]Current Patent Assignee: ADAMED SP. Z.O.O. - WO2010/133457, 2010, A1 Location in patent: Page/Page column 16-17
[2]Current Patent Assignee: ADAMED SP. Z.O.O. - US2012/65226, 2012, A1 Location in patent: Page/Page column 6

27
[ 283173-50-2 ]
[ 76-26-6 ]
CO-338 [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In water; isopropyl alcohol; at 70℃; for 0.166667h;	Example 17: Preparation of a1 R:1 S-Camsylate Salt.A slurry of Compound 1 (1 .5 g) was prepared in isopropyl alcohohwater (25 ml40:60 percent v/v). R-camphor sulfonic acid (0.65 g) and S-camphor sulfonic acid (0.65g) were added, as a solution, in water (1 .5 ml_). The slurry was heated to 70 °C over a 10 minute period. The resultant solution was cooled to 0 °C over a 10 minute period. Solid crystallized after holding this solution at a temperature of 0 °C for one hour. This resulted in the formation of a slurry. This slurry was granulated for a total of 36 hours. The crystals were filtered and washed with water and then dried overnight at 50 °C providing a pale yellow powder (1.9 g).

Reference： [1]Patent: WO2011/98971,2011,A1 .Location in patent: Page/Page column 87

28
9-methyl-3-oxa-9-azatricyclo[3.3.1.0(2,4)]non-7-yl hydroxy(di-2-thienyl)acetate [ No CAS ]
[ 5872-08-2 ]
C₁₀H₁₅O₄S^(1-)*C₁₉H₂₂NO₄S₂⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
80%	In dichloromethane; acetonitrile at 20℃; for 24h;	12 Example 12 Tiotropium salt with (+/-)-10-camphorsulphonic acid (anhydrous) 9-Methyl-3-oxa-9-azatricyclo[3.3.1.02,4]non-7-yl hydroxy(di-2-thienyl) acetate (0.1 mol ) was suspended in a mixture of methylene chloride /acetonitrile (76 ml : 115 ml ; 1:1.5 v/v). To the mixture methyl (+/-)-10-camphorsulphonate (0.5 mol ) in 73 ml of acetonitrile was added. Reaction was carried out for 24 h at room temperature . Then the reaction mixture was concentrated by evaporation until crystals precipitated and the obtained crystals were triturated in acetone , filtered off and dried in vacuum dryer at 30° C . Yield: 80% , HPLC purity: 99.70% .FIG. 3 shows XRPD pattern of the salt obtained above and Table 3 presents a detailed list of peaks with their relative intensities..

Reference： [1]Current Patent Assignee: ADAMED SP. Z.O.O. - US2012/65226, 2012, A1 Location in patent: Page/Page column 8

29
[ 124620-88-8 ]
[ 5872-08-2 ]
cis-2-methylspiro(1,3-oxathiolane-5,3')quinuclidine camphorsulfonic acid salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
12.04 g	In methanol; toluene at 20℃; for 22h;	16 Example 16 Preparation of cis-2-methylspiro(1,3-oxathiolane-5,3′)quinuclidine camphor-sulfonic acid salt To a solution of the epoxide of 3-methylenequinuclidine (10.79 g, 77.5 mmol) and acetyl thioethoxyethylacetal (12.06 g, 81.4 mmol) in toluene (100 mL) was added methanol (55 mL) and the reaction mixture was cooled to 0-5° C. Potassium tert-butoxide (0.87 g, 7.75 mmol) was then added and the reaction was maintained at 0-5° C. for 15 minutes before warming to room temperature for an additional 2 hours. The reaction mixture was then concentrated under reduced pressure. Toluene (110 mL) was added and the reaction was again concentrated under reduced pressure to 110 mL total volume. The reaction was cooled to 0-5° C. and trifluoroacetic acid (88.37 g, 775 mmol) was slowly added over 30 minutes. The reaction was maintained at 0-5° C. for an additional 30 minutes before warming to room temperature for 16 hours. The reaction was then cooled to 5-10° C. and slowly charged with 50% sodium hydroxide solution (62.0 g, 775 mmol). The biphasic mixture was transferred to a separatory funnel and the aqueous phase was adjusted to pH=12 by the addition of 50% sodium hydroxide solution (5 mL). The liquid phases were separated and the aqueous phase was extracted with toluene (4×33 mL), the organic extracts were combined and washed with water (1×10 mL). The organic extract was then concentrated to 105 mL, methanol (1.69 g, 52.8 mmol) and (+/-)-camphorsulfonic acid (8.83 g, 38.0 mmol) were charged to the reaction and the mixture was stirred at room temperature for 22 hours. The white precipitate which formed was collected by filtration, washed with toluene (2×11 mL) and dried under vacuum at room temperature to give 2-methylspiro(1,3-oxathiolane-5,3′) quinuclidine camphorsulfonic acid salt (12.04 g, 27.9 mmol, 36%) as a 95:5 mixture of cis:trans isomers as determined by 1H NMR. [0097] 1H NMR (400 MHz, CDCl3, cis-isomer) δ 5.16 (q, J=5.9 Hz, 1H), 3.57-3.41 (m, 4H), 3.39-3.30 (m, 2H), 3.27 (d, J=11.2 Hz, 1H), 3.22 (d, J=14.4 Hz, 1H), 3.03 (d, J=11.2 Hz, 1H), 2.83 (d, J=14.4 Hz, 1H), 2.61-2.53 (m, 1H), 2.41-2.39 (M, 1H), 2.34-2.27 (m, 1H), 2.21-2.13 (m, 4H), 2.06-1.78 (m, 3H), 1.57 (d, J=5.7 Hz, 3H), 1.42-1.36 (m, 1H), 1.05 (s, 3H), 0.83 (s, 3H)

Reference： [1]Current Patent Assignee: APOTEX INC - US2013/274474, 2013, A1 Location in patent: Paragraph 0096-0097

30
[ 76-26-6 ]
[ 1374640-70-6 ]
C₂₇H₂₈F₃N₇O₃*C₁₀H₁₆O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetone;	For each counterion and solvent system, ca. 25 or 50 mg of the free base of Compound 1 was slurried in 200-300 mu of the allocated solvent. The solvents included acetone, dichloromethane, cyclohexane, ethyl acetate, methanol (methyl ethyl ketone for sulfonic acid-containing counterions), methyl isobutyl ketone, 2-propanol (isopropyl acetate for sulfonic acid-containing counterions), tetrahydrofuran and acetonitrile:water (90: 10). The respective counterion was also dissolved / slurried in 200-300 mu of the allocated solvent. The counterions included benzenesulfonic acid, camphor sulfonic acid, 1,2-ethane disulfonic acid, hydrobromic acid, hydrochloric acid, maleic acid, methanesulfonic acid, naphthalene-2- sulfonic acid, 1,5 -naphthalene disulfonic acid, oxalic acid, 4-toluenesulfonic acid and 2,4,6- trihydroxybenzoic acid. One equivalent of each counterion was used and additional experiments with two equivalents of benzenesulfonic acid, hydrochloric acid, sulphuric acid and p-toluenesulfonic acid were performed. The acid solution / slurry was then added to the slurry of Compound 1 in small aliquots in order to minimize the risk of degradation. The pH of the reaction was then checked using universal indicator paper. The mixtures of Compound 1/counterion/solvent created using the procedure above were temperature cycled between ca. 0C and ambient (ca. 22C) whilst stirring in 1 hour cycles for a period of 1-2 days. Overnight, samples were kept at ca. 2-5C. The mixtures were visually checked for any obvious signs of degradation (i.e. color changes) and then, if not visually degraded, any solids present were isolated and allowed to dry at ambient conditions prior to analysis. The solids represent isolated Compound 2.

Reference： [1]Patent: WO2013/138502,2013,A1 .Location in patent: Paragraph 00219; 00220; 00232

31
[ 76-26-6 ]
[ 1374640-70-6 ]
C₂₇H₂₈F₃N₇O₃*2C₁₀H₁₆O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In acetone;	For each counterion and solvent system, ca. 25 or 50 mg of the free base of Compound 1 was slurried in 200-300 mu of the allocated solvent. The solvents included acetone, dichloromethane, cyclohexane, ethyl acetate, methanol (methyl ethyl ketone for sulfonic acid-containing counterions), methyl isobutyl ketone, 2-propanol (isopropyl acetate for sulfonic acid-containing counterions), tetrahydrofuran and acetonitrile:water (90: 10). The respective counterion was also dissolved / slurried in 200-300 mu of the allocated solvent. The counterions included benzenesulfonic acid, camphor sulfonic acid, 1,2-ethane disulfonic acid, hydrobromic acid, hydrochloric acid, maleic acid, methanesulfonic acid, naphthalene-2- sulfonic acid, 1,5 -naphthalene disulfonic acid, oxalic acid, 4-toluenesulfonic acid and 2,4,6- trihydroxybenzoic acid. One equivalent of each counterion was used and additional experiments with two equivalents of benzenesulfonic acid, hydrochloric acid, sulphuric acid and p-toluenesulfonic acid were performed. The acid solution / slurry was then added to the slurry of Compound 1 in small aliquots in order to minimize the risk of degradation. The pH of the reaction was then checked using universal indicator paper. The mixtures of Compound 1/counterion/solvent created using the procedure above were temperature cycled between ca. 0C and ambient (ca. 22C) whilst stirring in 1 hour cycles for a period of 1-2 days. Overnight, samples were kept at ca. 2-5C. The mixtures were visually checked for any obvious signs of degradation (i.e. color changes) and then, if not visually degraded, any solids present were isolated and allowed to dry at ambient conditions prior to analysis. The solids represent isolated Compound 2.

Reference： [1]Patent: WO2013/138502,2013,A1 .Location in patent: Paragraph 00219; 00220; 00232

32
[ 5872-08-2 ]
[ 3144-16-9 ]
[ 35963-20-3 ]

Yield	Reaction Conditions	Operation in experiment
	With barium(II) perchlorate In methanol Resolution of racemate;

Reference： [1]Smuts, Jonathan P.; Hao, Xin-Qi; Han, Zhaobin; Parpia, Curran; Krische, Michael J.; Armstrong, Daniel W. [Analytical Chemistry, 2014, vol. 86, # 2, p. 1282 - 1290]

33
[ 5872-08-2 ]
C₁₆H₁₈IO₂⁽¹⁺⁾*Br^(1-) [ No CAS ]
C₁₆H₁₈IO₂⁽¹⁺⁾*C₁₀H₁₅O₄S^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Stage #1: 10-camphorsufonic acid With silver(l) oxide In acetonitrile at 23℃; for 1h; Stage #2: C₁₆H₁₈IO₂⁽¹⁺⁾*Br^(1-) In acetonitrile at 23℃; for 12h;	2 Example 2: Synthesis of a salt represented by the formula (I-8) 5.00 parts of the compound represented by the formula (I-8-a) and 25 parts of acetonitrile were charged and after stirring at 23 ° C. for 30 minutes,2.49 parts of silver oxide was charged,After stirring at 23 ° C. for 1 hour,It was filtered.9.68 parts of the compound represented by the formula (I-8-c) was charged in the recovered filtrate,Followed by stirring at 23 ° C. for 12 hours.After filtering the obtained reaction mass,The collected filtrate was concentrated.To the collected residue,100 parts of chloroform and 35 parts of ion exchanged water were added and stirred at 23 ° C. for 30 minutes,The liquid was separated and the organic layer was taken out.Ion exchanged water (35 parts) was added to the recovered organic layer, and the mixture was stirred at 23 ° C. for 30 minutes,The liquid was separated and the organic layer was taken out.This washing operation was repeated 5 times.After concentrating the obtained organic layer,50 parts of tert-butyl methyl ether was added to the obtained residue, followed by stirring, followed by filtration,12.11 parts of a salt represented by the formula (I-8-d) was obtained.

Reference： [1]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED - JP6244891, 2017, B2 Location in patent: Paragraph 0222

34
[ 5872-08-2 ]
C₁₆H₁₈IO₂⁽¹⁺⁾*Br^(1-) [ No CAS ]
C₁₀H₁₅O₄S^(1-)*C₁₂H₁₇O₂S⁽¹⁺⁾ [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	Multi-step reaction with 2 steps 1.1: silver(l) oxide / acetonitrile / 1 h / 23 °C 1.2: 12 h / 23 °C 2.1: copper(II) benzoate / chlorobenzene / 1 h / 100 °C

Reference： [1]Current Patent Assignee: Sumitomo Chemical (w/o Dongwoo Fine-Chem); SUMITOMO CHEMICAL COMPANY LIMITED - JP6244891, 2017, B2

35
[ 5872-08-2 ]
[ 19231-06-2 ]
C₁₄H₁₄IO₂⁽¹⁺⁾*C₁₀H₁₅O₄S^(1-) [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
		5.00 parts of the compound represented by the formula (I-2-a) and 25 parts of acetonitrile,After stirring at 23 C. for 30 minutes,2.49 parts of silver oxide was charged,After stirring at 23 C. for 1 hour,It was filtered.9.08 parts of the compound represented by the formula (I-2-c) was charged in the recovered filtrate,Followed by stirring at 23 C. for 12 hours.After filtering the obtained reaction mass,The collected filtrate was concentrated.To the collected residue,100 parts of chloroform and 35 parts of ion exchanged water were added and stirred at 23 C. for 30 minutes,The liquid was separated and the organic layer was taken out.Ion exchanged water (35 parts) was added to the recovered organic layer, and the mixture was stirred at 23 C. for 30 minutes,The liquid was separated and the organic layer was taken out.This washing operation was repeated 5 times.After concentrating the obtained organic layer,To the obtained residue,After adding 50 parts of tert-butyl methyl ether and stirring,By filtration, 11.69 parts of a salt represented by the formula (I-2-d) was obtained.

Reference： [1]Patent: JP6244891,2017,B2 .Location in patent: Paragraph 0218

36
[ 5872-08-2 ]
C₇H₁₂N₂O₃S [ No CAS ]
2-methyl-3-(3-sulfopropyl)imidazolium camphorsulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 85 - 90℃;	General procedure: After drying, the zwitterions (0.1 mol) were further taken in equimolar concentration with 10-camphorsulfonic acid, abbreviated as CSA, (0.1 mol) at 85-90 °C for 4-6 h [25-27]. The ILs formed were washed with diethylether and ethyl acetate and were dried under vacuum at 70 °C for 24 h. The general synthetic route for synthesis of PILs is shown in Fig. 1. The synthetic equations, showing detailed reaction conditions, for individual IL are provided in supporting information (Fig. S1).

Reference： [1]Sardar, Sabahat; Wilfred, Cecilia Devi; Mumtaz, Asad; Leveque, Jean-Marc; Khan, Amir Sada; Krishnan, Sooridarsan [Journal of Molecular Liquids, 2018, vol. 269, p. 178 - 186]

37
[ 5872-08-2 ]
C₈H₁₄N₂O₃S [ No CAS ]
2-ethyl-3-(3-sulfopropyl)imidazolium camphorsulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 85 - 90℃;	General procedure: After drying, the zwitterions (0.1 mol) were further taken in equimolar concentration with 10-camphorsulfonic acid, abbreviated as CSA, (0.1 mol) at 85-90 °C for 4-6 h [25-27]. The ILs formed were washed with diethylether and ethyl acetate and were dried under vacuum at 70 °C for 24 h. The general synthetic route for synthesis of PILs is shown in Fig. 1. The synthetic equations, showing detailed reaction conditions, for individual IL are provided in supporting information (Fig. S1).

Reference： [1]Sardar, Sabahat; Wilfred, Cecilia Devi; Mumtaz, Asad; Leveque, Jean-Marc; Khan, Amir Sada; Krishnan, Sooridarsan [Journal of Molecular Liquids, 2018, vol. 269, p. 178 - 186]

38
[ 5872-08-2 ]
C₁₂H₁₄N₂O₃S [ No CAS ]
2-phenyl-3-(3-sulfopropyl)imidazolium camphorsulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 85 - 90℃;	General procedure: After drying, the zwitterions (0.1 mol) were further taken in equimolar concentration with 10-camphorsulfonic acid, abbreviated as CSA, (0.1 mol) at 85-90 °C for 4-6 h [25-27]. The ILs formed were washed with diethylether and ethyl acetate and were dried under vacuum at 70 °C for 24 h. The general synthetic route for synthesis of PILs is shown in Fig. 1. The synthetic equations, showing detailed reaction conditions, for individual IL are provided in supporting information (Fig. S1).

Reference： [1]Sardar, Sabahat; Wilfred, Cecilia Devi; Mumtaz, Asad; Leveque, Jean-Marc; Khan, Amir Sada; Krishnan, Sooridarsan [Journal of Molecular Liquids, 2018, vol. 269, p. 178 - 186]

39
C₁₀H₁₂N₂O₃S [ No CAS ]
[ 5872-08-2 ]
3-(3-sulfopropyl)benzimidazolium camphorsulfonate [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	at 85 - 90℃;	General procedure: After drying, the zwitterions (0.1 mol) were further taken in equimolar concentration with 10-camphorsulfonic acid, abbreviated as CSA, (0.1 mol) at 85-90 °C for 4-6 h [25-27]. The ILs formed were washed with diethylether and ethyl acetate and were dried under vacuum at 70 °C for 24 h. The general synthetic route for synthesis of PILs is shown in Fig. 1. The synthetic equations, showing detailed reaction conditions, for individual IL are provided in supporting information (Fig. S1).

Reference： [1]Sardar, Sabahat; Wilfred, Cecilia Devi; Mumtaz, Asad; Leveque, Jean-Marc; Khan, Amir Sada; Krishnan, Sooridarsan [Journal of Molecular Liquids, 2018, vol. 269, p. 178 - 186]

40
[ 5872-08-2 ]
C₁₃H₂₁NO₂ [ No CAS ]
C₁₂H₂₀N₂O₂*C₁₀H₁₆O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform-d1

Reference： [1]Feng, Si; Yao, Liangyuan; Liu, Fengliang; Zeng, Xiao; Wang, Junjie [Tetrahedron Letters, 2018, vol. 59, # 49, p. 4305 - 4310]

41
[ 5872-08-2 ]
C₁₅H₂₅NO₂ [ No CAS ]
C₁₅H₂₅NO₂*C₁₀H₁₆O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform-d1

Reference： [1]Feng, Si; Yao, Liangyuan; Liu, Fengliang; Zeng, Xiao; Wang, Junjie [Tetrahedron Letters, 2018, vol. 59, # 49, p. 4305 - 4310]

42
[ 5872-08-2 ]
C₁₇H₁₉F₃N₂O₂ [ No CAS ]
C₁₇H₁₉F₃N₂O₂*C₁₀H₁₆O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform-d1

Reference： [1]Feng, Si; Yao, Liangyuan; Liu, Fengliang; Zeng, Xiao; Wang, Junjie [Tetrahedron Letters, 2018, vol. 59, # 49, p. 4305 - 4310]

43
[ 5872-08-2 ]
C₁₈H₂₁F₃N₂O₂ [ No CAS ]
C₁₈H₂₁F₃N₂O₂*C₁₀H₁₆O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform-d1

Reference： [1]Feng, Si; Yao, Liangyuan; Liu, Fengliang; Zeng, Xiao; Wang, Junjie [Tetrahedron Letters, 2018, vol. 59, # 49, p. 4305 - 4310]

44
[ 5872-08-2 ]
C₁₉H₂₅NO₂ [ No CAS ]
C₁₈H₂₄N₂O₂*C₁₀H₁₆O₄S [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In chloroform-d1

Reference： [1]Feng, Si; Yao, Liangyuan; Liu, Fengliang; Zeng, Xiao; Wang, Junjie [Tetrahedron Letters, 2018, vol. 59, # 49, p. 4305 - 4310]

45
[ 283173-50-2 ]
[ 5872-08-2 ]
8-fluoro-2-{4-[(methylamino)methyl]phenyl}-1,3,4,5-tetrahydro-6H-azepino[5,4,3-cd]indol-6-one ((1S,4R)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl)methanesulfonic acid salt [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
	In 1,2-dimethoxyethane; water; at 30℃; for 5h;	<strong>[283173-50-2]Rucaparib</strong> base (0.1 g) and DL-10-camphorsulfonic acid (0.072 g) were dissolved in a 1,2-dimethoxy ethane and water mixture (1:1; 3 mL) at 30 C. The clear reaction mass was filtered to remove the undissolved particulates and stirred at 30 C. for 5 h. The resulting product was filtered, washed with isopropyl ether (1 mL) and dried at 40 C. under vacuum for 3 h. The resulting product was identified as crystalline <strong>[283173-50-2]rucaparib</strong> camsylate salt Form beta.

Reference： [1]Patent: US2019/233428,2019,A1 .Location in patent: Paragraph 0136

46
[ 881681-00-1 ]
[ 5872-08-2 ]
[ 1621259-58-2 ]

Yield	Reaction Conditions	Operation in experiment
85.8%	In methanol; ethyl acetate for 0.5h; Reflux;	3 Comparative Example 3:Preparation of camsylate of 1 -[5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1 H-pyrrol-3-yl]-N-methylmethanamine (vonoprazan) 2.0 g of 1-[5-(2-fluorophenyl)-1-(pyridin-3-ylsulfonyl)-1H-pyrrol-3-yl]-N-methylmethanamine (vonoprazan) in 6.0 mL of methyl alcohol And 50.0 mL of ethyl acetate were added, followed by addition of 1.35 g of camsylic acid. After stirring at reflux for 30 minutes, the mixture was cooled to room temperature and stirred for 12 hours. The obtained solid was filtered, washed with ethyl acetate, and dried to obtain 2.80 g of vonoprazan camsylate. (Yield 85.8%, purity 99.96%)

Reference： [1]Current Patent Assignee: ILDONG PHARMACEUTICAL CO.,LTD. - KR102222443, 2021, B1 Location in patent: Paragraph 0076-0078

47
[ 5872-08-2 ]
[ 2712-78-9 ]
[di((camphorsulfonyl)oxy)iodo]benzene [ No CAS ]