35963-20-3

Basic information

• Product Name: (1R)-(-)-10-Camphorsulfonic acid
• Synonyms: (1R)-(-)-CAMPHOR-10-SULPHONIC ACID;(1R)-(-)-CAMPHOR-10-SULFONIC ACID;(1R)-CAMPHOR-10-SULFONIC ACID;(1R)-(-)-CAMPHORSULFONIC ACID;(1r)-[7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulphonic acid;(1R)-(-)-10-CAMPHORSULFONIC ACID;(-)-10-CAMPHORSULFONIC ACID;(-)-CAMPHOR-10-SULPHONIC ACID
• CAS NO: 35963-20-3
• Molecular Formula: C₁₀H₁₆O₄S
• Molecular Weight: 232.3
• EINECS: 252-817-9
• Product Categories: FINE Chemical & INTERMEDIATES;Chiral Compounds;chiral;Bicyclic Monoterpenes;Biochemistry;for Resolution of Bases;Optical Resolution;Reagents for Oligosaccharide Synthesis;Synthetic Organic Chemistry;Terpenes;Peptide;Chiral Reagents;Intermediates & Fine Chemicals;Pharmaceuticals;Sulfur & Selenium Compounds
• Mol File: 35963-20-3.mol

Chemical Properties

• Melting Point: 198 °C (dec.)(lit.)
• Boiling Point: 344.46°C (rough estimate)
• Flash Point: 236.6°C
• Appearance: White to slightly beige/Crystalline Powder
• Density: 1.2981 (rough estimate)
• Vapor Pressure: 2.9E-10mmHg at 25°C
• Refractive Index: -21.5 ° (C=5, H2O)
• Storage Temp.: 2-8°C
• PKA: 1.17±0.50(Predicted)
• Water Solubility: soluble
• Sensitive: Hygroscopic
• Stability: Stable. Hygroscopic. Incompatible with strong bases, strong oxidizing agents.
• BRN: 2809676
• CAS DataBase Reference: (1R)-(-)-10-Camphorsulfonic acid(CAS DataBase Reference)
• NIST Chemistry Reference: (1R)-(-)-10-Camphorsulfonic acid(35963-20-3)
• EPA Substance Registry System: (1R)-(-)-10-Camphorsulfonic acid(35963-20-3)

Safety Data

• Hazard Codes: C
• Statements: 34
• Safety Statements: 26-36/37/39-45-24/25-27
• RIDADR: UN 3261 8/PG 2
• WGK Germany: 3
• F: 3-10
• TSCA: Yes
• HazardClass: 8
• PackingGroup: III
• Hazardous Substances Data: 35963-20-3(Hazardous Substances Data)

Usage

L-Camphorsulfonic acid

Camphor sulfonic acid includes L-camphor sulfonic acid, D-camphor sulfonic acid and racemic camphor sulfonic acid these three isomers. It is a kind of white columnar crystals with the melting point of 193°C (decomposition). [α]D20+24° (water). It is Slightly soluble in ethanol, insoluble in ether, soluble in sodium hydroxide and sodium carbonate solution. L-camphor sulfonic acid could be produced from reaction between camphor, sulfuric acid and acetic anhydride.It has a lot of functions such as exciting the respiratory center, the vascular movement center and myocardium. Its sodium salt plays pharmaceutical role in medicine. Camphor sulfonic acid sodium salt is a kind of white crystalline powder. It is odorless and tastes bitter and then sweet. It is easily absorb moisture and easily dissolve in the water and hot ethanol. So it should be shading confined preservation. it can Directly excite the medulla oblongata respiratory center and vascular movement center, and quicken and deepen the breath, rise the blood pressure; it also can directly excite the myocardium and strength the contraction of cardiac muscle as well as could increase the output. It is applied the treatment of infectious disease, as well as the disease like central inhibition of poisoning caused by respiratory depression, fatigue, high fever, poisoning, heat stroke and other acute heart failure.

Uses

Different sources of media describe the Uses of 35963-20-3 differently. You can refer to the following data:
1. (1) It is also used for the racemization of optical isomers. (2) It can be applied to the resolution of intermediate or isomer in medicine. (3) It also could play a role as organic synthesis intermediates and resolving agent.
2. 1R)-(-)-10-Camphorsulfonic acid is a chiral derivative of Camphor.It has the following uses: (1)It is also used for the racemization of optical isomers. (2) It can be applied to the resolution of intermediate or isomer in medicine. (3) It also could play a role as organic synthesis intermediates and resolving agent.
3. (1R)-(-)-Camphor-10-sulfonic acid, is used as a pharamaceutical intermediate and also used as a chiral derivative of Camp. It can also be used as resolving agents for chiral amines and other cations.

Production method

Camphor sulfonic acid is obtained from camphor and sulfuric acid by irradiation. This method involves: 1) Adding the camphor and acetic anhydride to the pot. 2) Mixing it and making it dissolved. 3) Dripping sulfuric acid after cooling. And the reaction should be maintained at 44-45 °C for 48 hours. Then cool it to 6-7 °C. 4) Crystallizing, filtrating, washing with a small amount of acetic acid crystals, and dry it to get camphor sulfonic acid.

Physical properties

(1R)-(-)-10-Camphorsulfonic acid is a kind of prismatic crystals and its melting point is 193-195 ° C (decompose). It is Insoluble in ether and slightly soluble in glacial acetic acid and ethyl acetate. And it is and moisture in wet air.

Definition

ChEBI: The R enantiomer of camphorsulfonic acid.

General Description

(1R)-(-)-10-Camphorsulfonic acid is an HPLC derivatization reagent for UV/Vis detection. It is mainly employed for the resolution of bases.

Purification Methods

It forms prisms from AcOH or EtOAc, and is deliquescent in moist air. Store it in tightly stoppered bottles. The NH4 salt forms needles from H2O [] D ±20.5o (c 5, H2O). [Burgess & Lowry J Chem Soc 127 279 1925, Marsi et al. J Am Chem Soc [ 78 3063 1956.] The RS-acid recrystallises from AcOH. [60g of (±)-acid in 60mL of AcOH at 105o gave 40g of crystals has m 202-203o [Bartlett & Knox Org Synth 45 12 1965.] [Beilstein 11 IV 642.]

InChI:InChI=1/C10H16O4S.H2O/c1-9(2)7-3-4-10(9,8(11)5-7)6-15(12,13)14;/h7H,3-6H2,1-2H3,(H,12,13,14);1H2

Synthetic route

(2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1R)-10-camphorsulfonate (188416-34-4, 137234-71-0) → (R)-10-camphorsulfonic acid (35963-20-3)

Conditions	Yield
Stage #1: (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1R)-10-camphorsulfonate With potassium carbonate In dichloromethane; water pH=8.9; Stage #2: In dichloromethane; cyclohexane at 20 - 50℃; for 8h; Reagent/catalyst;	93.2%

brucine (357-57-3) + 10-camphorsufonic acid (5872-08-2) → (1S)-10-camphorsulfonic acid (3144-16-9) + (R)-10-camphorsulfonic acid (35963-20-3)

10-camphorsufonic acid (5872-08-2) → (R)-10-camphorsulfonic acid (35963-20-3)

Conditions	Yield
With hydrogenchloride; d-phenylglycine
With brucine

camphor-10-sulfonic acid (76-26-6, 3144-16-9, 5872-08-2, 35963-20-3) → (R)-10-camphorsulfonic acid (35963-20-3)

brucine salt of/the/ -β-sulfonic acid → (R)-10-camphorsulfonic acid (35963-20-3)

Conditions	Yield
man zerlegt das in der Mutterlauge vom Brucinsalz der d-Saeure vorgekommene Salz mit Barytwasser;

l-camphor → (R)-10-camphorsulfonic acid (35963-20-3)

Conditions	Yield
With sulfuric acid; acetic anhydride

hydrogenchloride (7647-01-0) + (S)-2-phenylglycine (2935-35-5) + 10-camphorsufonic acid (5872-08-2) → (1S)-10-camphorsulfonic acid (3144-16-9) + (R)-10-camphorsulfonic acid (35963-20-3)

d-camphor β-sulphonate ammonium salt (82509-30-6) → (R)-10-camphorsulfonic acid (35963-20-3)

Conditions	Yield
In water; 4-methyl-2-pentanone at 80 - 117℃; Inert atmosphere;

10-camphorsufonic acid (5872-08-2) → (1S)-10-camphorsulfonic acid (3144-16-9) + (R)-10-camphorsulfonic acid (35963-20-3)

Conditions	Yield
With barium(II) perchlorate In methanol Solvent; Reagent/catalyst; Resolution of racemate;

(R)-10-camphorsulfonic acid (35963-20-3) + 4-(1H-imidazol-1-yl)-2-butanone (59543-81-6) → 1-(3'-oxobutyl)imidazolium (+)-camphor-10-sulfonate

Conditions	Yield
In dichloromethane at 0℃; for 2h; Inert atmosphere;	100%

(R)-10-camphorsulfonic acid (35963-20-3) + triphenylbismuthane (603-33-8) → Bi(3+)*3C10H15O4S(1-)

Conditions	Yield
In neat (no solvent) at 85℃; for 4h;	100%

(R)-10-camphorsulfonic acid (35963-20-3) + (2S*,3R*,3'R*,4'R*)-2-(3',4'-epoxy-5'-hexenyl)tetrahydropyran-3-ol (121352-80-5, 121422-48-8) → ((1R,4S)-7,7-Dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-methanesulfonic acid (1R,2R)-2-hydroxy-4-((2S,3R)-3-hydroxy-tetrahydro-pyran-2-yl)-1-vinyl-butyl ester (121352-81-6)

Conditions	Yield
In dichloromethane for 0.5h; Ambient temperature;	98%

(R,E)-methyl 2-(3-(acetylthio)-3-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)propyl)benzoate (855473-48-2) + (R)-10-camphorsulfonic acid (35963-20-3) + methylmagnesium chloride (676-58-4) → (R,E)-2-[2-(3-{3-[2-(7-chloro-quinolin-2-yl)-vinyl]-phenyl}-3-mercapto-propyl)-phenyl]-propan-2-ol (R)-camphorsulfonate

Conditions	Yield
Stage #1: methylmagnesium chloride With cerium(III) chloride In tetrahydrofuran at -20 - 25℃; for 1.75h; Stage #2: (R,E)-methyl 2-(3-(acetylthio)-3-(3-(2-(7-chloroquinolin-2-yl)vinyl)phenyl)propyl)benzoate In tetrahydrofuran; toluene at -20℃; for 0.5h; Stage #3: (R)-10-camphorsulfonic acid	97.65%

(R)-10-camphorsulfonic acid (35963-20-3) + silver(l) oxide (20667-12-3) → silver (1R)-(-)-camphor-10-sulfonate (99147-14-5)

Conditions	Yield
In water an aq. soln. of the camphorsulfonic acid was treated with silver oxide; stirring for 5 min;; centrifugation and decantation; the supernatant was evapd. to dryness; the residue was washed with cold H2O and dried under vac.;;	96.7%

[bis(acetoxy)iodo]benzene (3240-34-4) + (R)-10-camphorsulfonic acid (35963-20-3) → [hydroxy[((1R)-10-camphorylsulfonyl)oxy]iodo]benzene

Conditions	Yield
for 0.00555556h; Microwave irradiation; neat (no solvent);	94%
for 0.166667h;	91%

(R)-10-camphorsulfonic acid (35963-20-3) + naphthalen-1-yl-λ3-iodanediyl diacetate (41018-45-5) → C20H23IO5S

Conditions	Yield
for 0.166667h;	94%

TC-5619 (639489-84-2) + (R)-10-camphorsulfonic acid (35963-20-3) → (2S,3R)-N-(2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]oct-3-yl)benzofuran-2-carboxamide R-camphorsulfonate (1111941-97-9)

Conditions	Yield
In ethanol Heating / reflux;	93.8%

Cyclohexyl isocyanide (931-53-3) + (R)-10-camphorsulfonic acid (35963-20-3) → N-cyclohexyl-C-(7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-methanesulfonamide

Conditions	Yield
With water In dichloromethane at 20℃; for 0.333333h;	93%

[2-(3-Methyl-3H-imidazol-4-yl)-thieno[3,2-b]pyridin-7-yl]-(2-methyl-1H-indol-5-yl)-amine (225382-63-8) + (R)-10-camphorsulfonic acid (35963-20-3) → C20H17N5S*C10H16O4S

Conditions	Yield
In tetrahydrofuran; methanol; dichloromethane Large scale;	93%

tert-butylisonitrile (119072-55-8, 7188-38-7) + (R)-10-camphorsulfonic acid (35963-20-3) → (R)-C-(7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-N-tert-butylmethanesulfonamide

Conditions	Yield
With water In dichloromethane at 20℃; for 0.333333h;	92%

methyl-1-(1,3-benzodioxol-5-yl)-2,3,4,9-tetrahydro-1H-β-carboline-3-carboxylate (82789-35-3) + (R)-10-camphorsulfonic acid (35963-20-3) → (1R,3R)-1-(3,4-methylenedioxyphenyl)-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic methyl ester (1R)-10-camphorsulfonic acid salt (1375000-23-9)

Conditions	Yield
In nitromethane at 0℃; Reflux;	92%

(R)-10-camphorsulfonic acid (35963-20-3) + dimethyl 2-((fluoromethyl)(phenyl)-l4-sulfaneylidene)malonate → fluoromethyl ((1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate

Conditions	Yield
In acetone at 40℃; for 0.0833333h; Schlenk technique; Inert atmosphere;	92%

4-vinyl benzylamine (1520-21-4) + (R)-10-camphorsulfonic acid (35963-20-3) → C10H16O4S*C8H9N

Conditions	Yield
In methanol; isopropyl alcohol at 0℃; for 1.5h;	92%

((2S,4S)-4-(4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl)pyrrolidin-2-yl)(1,3-thiazolidin-3-yl)methanone (760937-92-6) + (R)-10-camphorsulfonic acid (35963-20-3) → 3-{(2S,4S)-4-[4-(3-methyl-1-phenyl-1H-pyrazol-5-yl)piperazin-1-yl]pyrrolidin-2-ylcarbonyl}thiazolidine di-(-)-camphorsulfonate

Conditions	Yield
In tetrahydrofuran; tert-butyl methyl ether at 20℃; for 1h;	91%

(R)-10-camphorsulfonic acid (35963-20-3) → (+/-)-10-Camphorsulfonamide (72597-34-3)

Conditions	Yield
With ammonium hydroxide In dichloromethane at 0℃; for 2h;	90%
Stage #1: (R)-10-camphorsulfonic acid With thionyl chloride In chloroform for 17h; Heating / reflux; Stage #2: With ammonia In chloroform; water at 4 - 20℃; for 4h;	83%
Multi-step reaction with 2 steps 1: 80.5 percent / PCl5 / 1 h at 0 deg C and 2 h at r.t. 2: 74 percent / NH3 / toluene / 0 °C View Scheme

piperonal (120-57-0) + (R)-10-camphorsulfonic acid (35963-20-3) + DL-tryptophan methyl ester (7303-49-3) → (1R,3R)-1-(3,4-methylenedioxyphenyl)-2,3,4,9-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylic methyl ester (1R)-10-camphorsulfonic acid salt (1375000-23-9)

Conditions	Yield
In nitromethane at 0 - 30℃; Reflux;	90%

(R)-10-camphorsulfonic acid (35963-20-3) + 1-(2-methyl-3-chlorophenyl)-4,6-dimethylpyrimidin-2(1H)-thione (75276-67-4) → 1-(2-methyl-3-chlorophenyl)-4,6-dimethyl-2-thioxo-1,2-dihydropyrimidinium D-camphor-10-sulphonate (75276-78-7)

Conditions	Yield
In ethanol for 1h; Heating;	89%

(R)-10-camphorsulfonic acid (35963-20-3) + 1-β-dimethylaminoethyl-3,3-bis(trifluoromethyl)diaziridine (83391-98-4, 83435-51-2, 106036-93-5) → [2-(3,3-Bis-trifluoromethyl-diaziridin-1-yl)-ethyl]-dimethyl-amine; compound with ((1R,4S)-7,7-dimethyl-2-oxo-bicyclo[2.2.1]hept-1-yl)-methanesulfonic acid (83429-30-5)

Conditions	Yield
In isopropyl alcohol at 0℃; for 24h;	88.1%

(R)-10-camphorsulfonic acid (35963-20-3) + (S)-(+)-clopidogrel (113665-84-2) → clopidogrel (1R)-(-)-camphor-10-sulfonate

Conditions	Yield
In acetone at 20℃; for 12h;	88%
In acetone at 20℃; for 4h;	86%
In acetone at 25 - 56℃; for 2.5h;	85.25%
In ethyl acetate at 20℃; for 2h; Product distribution / selectivity;
In acetone at 20℃; for 2h; Product distribution / selectivity;

(R)-10-camphorsulfonic acid (35963-20-3) + C22H27FN4O3 → C10H16O4S*C17H19FN4O

Conditions	Yield
In water; acetonitrile at 60℃; for 4.5h; Solvent; Inert atmosphere; Large scale;	88%

(R)-10-camphorsulfonic acid (35963-20-3) + triphenylbismuth(V) diacetate (28899-97-0) → triphenylbismuth bis[(1R)-(-)-camphor-10-sulfonate]

Conditions	Yield
In acetonitrile addn. of soln. of (1R)-(-)-camphor-10-sulfonic acid (2 equiv.) in MeCN to soln. of Bi(OAc)2Ph3 (1 equiv.) in MeCN; reflux with stirring for 1 h; filtration, removal of solvent under reduced pressure, recrystn. from CH2Cl2-Et2O-pentane; elem. anal.;	86%

(R)-10-camphorsulfonic acid (35963-20-3) → [(1R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl]methanesulfonyl azide

Conditions	Yield
With sodium azide; trichloroacetonitrile; triphenylphosphine In acetonitrile at 20℃; for 2h;	86%

(R)-butane-1,3-diol (6290-03-5) + (R)-10-camphorsulfonic acid (35963-20-3) + Benzhydrylamine (91-00-9) → (2S)-1-(diphenylmethyl)-2-methylazetidinium [(1R,4S)-7,7-dimethyl-2-oxobicyclo[2.2.1]hept-1-yl]methanesulfonate

Conditions	Yield
Stage #1: (R)-butane-1,3-diol With trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine In acetonitrile at -35 - -30℃; for 3.83333h; Inert atmosphere; Stage #2: Benzhydrylamine In acetonitrile at -35 - 45℃; for 2.66667h; Stage #3: (R)-10-camphorsulfonic acid In methanol at 10 - 20℃; for 0.25h;	86%
Stage #1: (R)-butane-1,3-diol With trifluoromethylsulfonic anhydride; N-ethyl-N,N-diisopropylamine In acetonitrile at -35 - -30℃; for 0.833333h; Stage #2: (R)-10-camphorsulfonic acid; Benzhydrylamine In acetonitrile at -30 - 45℃;	65%

(R)-10-camphorsulfonic acid (35963-20-3) + 5-((R)-2-amino-1-propyl)-2-methoxybenzenesulphonamide (112101-81-2) → C10H16N2O3S*C10H16O4S (906338-31-6)

Conditions	Yield
In water; isopropyl alcohol at 0 - 4℃; for 1.5h; Product distribution / selectivity; Heating / reflux;	85.65%

(R)-5-(2-aminoethyl)-1-(6,8-difluorochroman-3-yl)-1,3-dihydroimidazole-2-thione + (R)-10-camphorsulfonic acid (35963-20-3) → (R)-5-(2-aminoethyl)-1-(6,8-difluorochroman-3-yl)-1,3-dihydroimidazole-2-thione camphorsulfonate

Conditions	Yield
In methanol at 20 - 50℃; for 2h; Product distribution / selectivity; Heating / reflux;	85%
In methanol; ethyl acetate at 20 - 50℃; for 2h; Product distribution / selectivity; Heating / reflux;
In methanol; isopropyl alcohol at 20 - 50℃; for 2h; Product distribution / selectivity; Heating / reflux;

Trimethyl orthoacetate (1445-45-0) + (R)-10-camphorsulfonic acid (35963-20-3) → methyl 1R-(-)-10-camphorsulphonate (83603-04-7)

Conditions	Yield
In dichloromethane at 20℃;	85%
at 20℃;	85%

4-Chloro-6-fluoroquinoline (391-77-5) + ethyl 4-oxocyclohexane-1-carboxylate (17159-79-4) + (R)-10-camphorsulfonic acid (35963-20-3) → 4-(6-fluoroquinolin-4-yl)cyclohexan-1-one ((1R)-7,7-dimethyl-2-oxobicyclo[2.2.1]heptan-1-yl)methanesulfonate

Conditions	Yield
Stage #1: ethyl 4-oxocyclohexane-1-carboxylate; (R)-10-camphorsulfonic acid In ethylene glycol; toluene at 60℃; for 4h; Inert atmosphere; Dean-Stark; Large scale; Stage #2: 4-Chloro-6-fluoroquinoline With sodium hexamethyldisilazane In tetrahydrofuran; N,N-dimethyl-formamide; toluene at -20℃; for 3h; Large scale; Stage #3: In ethylene glycol Temperature; Large scale;	84.8%

(R)-10-camphorsulfonic acid (35963-20-3) + clopidogrel (90055-48-4) → (+)-clopidogrel camphorsulfonic acid

Conditions	Yield
In 1,2-dichloro-ethane at 20℃; for 53h; Product distribution / selectivity;	84.7%
In ethyl acetate at 20℃; for 53h; Product distribution / selectivity;	83.8%
In isopropyl alcohol at 20 - 35℃; for 53h; Product distribution / selectivity;	82.9%

Upstream product

• 736109-58-3 1,7,7-trimethyl-bicyclo[2.2.1]heptan-2-one 
• 357-57-3 brucine 
• 5872-08-2 10-camphorsufonic acid 
• 76-26-6 camphor-10-sulfonic acid 
• 7647-01-0 hydrogenchloride 
• 2935-35-5 (S)-2-phenylglycine 
• 82509-30-6 d-camphor β-sulphonate ammonium salt 
• 188416-34-4 (2R,3S)-2-(2,4-difluorophenyl)-3-(5-fluoro-4-pyrimidinyl)-1-(1H-1,2,4-triazol-1-yl)-2-butanol (1R)-10-camphorsulfonate 

Downstream Products

• 3144-16-9 (1S)-10-camphorsulfonic acid 
• 35963-20-3 (R)-10-camphorsulfonic acid 
• 367522-55-2 7,7-dimethyl-2,3-dioxo-bicyclo[2.2.1]heptane-4-methanesulfonic acid 
• 295788-95-3 8-[2,4-Bis(methoxymethoxy)phenyl]-1,4-dioxaspiro[4.5]dec-7-ene 
• 464-78-8 ketopinic acid 
• 165806-94-0 N-[(4-fluorophenyl)[(4-methylphenyl)sulfonyl]methyl]formamide 
• 10413-17-9 6-phenyltetrahydropyran-2-one 
• 676165-94-9 N-[benzo[1,3]dioxol-5-yl-(toluene-4-sulfonyl)-methyl]-formamide 
• 847448-60-6 4-chloro-2-(tetrahydro-pyran-2-yl)-2H-pyrazolo[3,4-d]pyrimidine 
• 91446-15-0 4-chloro-1-(tetrahydro-2H-pyran-2-yl)-1H-pyrazolo[3,4-d]-pyrimidine 
• 579475-69-7 2-(4-fluoro-2-methylphenyl)-4-piperidinone camphor-10-sulfonate 
• 114214-50-5 3-hydroxy-4-methoxy-pyrrolidine-1-carboxylic acid tert-butyl ester 
• 368835-52-3 6-Ethyl-3,3-dimethoxy-2-phenyl-2,3,4,5-tetrahydro-pyridine camphorsulfonate 
• 374886-53-0 3-[3-(3-Methoxypropyl)-5-(6-phenylpyridin-3-yl)-4H-1,2,4-triazol-4-yl]-2-methylbenzamide 

Relevant articles and documents

Voriconazole resolving agent (R)-10 - camphor sulfonic acid recovery method

The invention discloses a Voriconazole resolving agent (R)- 10 - camphorsulfonic acid recovery method, comprises the following steps: (1) alkali treatment: the Voriconazole is soluble in methylene chloride and water camphor sulfonate in the mixed solution of, adding alkali treatment of weak base aqueous solution, to be delaminated separation, keeps the water level for use; (2) the acidification process: in step (1) by adding a strong acid in the aqueous layer of the acidification process, then the concentration and evaporation drying to get the solid; the resulting solid under the heating condition is dissolved in the organic solvent, filtering, remain filtrate for use; (3) crystallization processing: the cyclohexane are added to step (2) in the filtrate obtained by, cooling crystallization, crystallization carried out upon completion of filtering, to obtain the (R)- 10 - camphorsulfonic acid. Voriconazole resolving agent (R)- 10 - camphorsulfonic acid recovery method has a simple separation, separation product has high optical purity, economic, environmental protection and the like.

Enantiomeric separations of chiral sulfonic and phosphoric acids with barium-doped cyclofructan selectors via an ion interaction mechanism

New cyclofructan-6 (CF6)-based chiral stationary phases (CSPs) bind barium cations. As a result, the barium-complexed CSPs exhibit enantioselectivity toward 16 chiral phosphoric and sulfonic acids in the polar organic mode (e.g., methanol or ethanol mobile phase containing a barium salt additive). Retention is predominantly governed by a strong ionic interaction between the analyte and the complexed barium cation as well as hydrogen bonding with the cyclofructan macrocycle. The log k versus log [X], where [X] = the concentration of the barium counteranion, plots for LARIHC-CF6-P were linear with negative slopes demonstrating typical anion exchange behavior. The nature of the barium counteranion also was investigated (acetate, methanesulfonate, trifluoroacetate, and perchlorate), and the apparent elution strength was found to be acetate > methanesulfonate > trifluoroacetate > perchlorate. A theory based upon a double layer model was proposed wherein kosmotropic anions are selectively adsorbed to the cyclofructan macrocycle and attenuate the effect of the barium cation. van't Hoff studies for two analytes were conducted on the LARIHC-CF6-P for three of the barium salts (acetate, trifluoroacetate, and perchlorate), and the thermodynamic parameters governing retention and enantioselectivity are discussed. Interestingly, for the entropically driven separations, enantiomeric selectivity can increase at higher temperatures, even with decreasing retention.

Identification of small molecule sulfonic acids as ecto-5'-nucleotidase inhibitors

Ecto-5'-Nucleotidase inhibitors have great potential as anti-tumor agents. We have investigated biochemical properties of human and rat ecto-5'-Nucleotidases and characterized 19 small molecule sulfonic acid derivatives as potential inhibitors of ecto-5'-Nucleotidases. We identified 11 potent inhibitors of human and rat ecto-5'-Nucleotidases and checked their selectivity. Compound 10 (Sodium 2,4-dinitrobenzenesulfonate) with Ki value of 0.66 μM and 19 (N-(4- sulfamoylphenylcarbamothioyl) pivalamide) with Ki value of 0.78 μM were identified as the most potent inhibitors for human and rat ecto-5'-Nucleotidase, respectively. The present compounds have low molecular weights, water solubility and equal potency as compared to the reported inhibitors.

Reactive Extraction of Free Organic Acids from the Ammonium Salts Thereof

The invention relates to a process for converting ammonium salts of organic acids to the particular free organic acid, wherein an aqueous solution of the ammonium salt is contacted with an organic extractant and the salt is dissociated at temperatures and pressures at which the aqueous solution and the extractant are in the liquid state, and a stripping medium or entraining gas is introduced in order to remove NH3 from the aqueous solution and transfer at least a portion of the free organic acid formed to the organic extractant. The invention described here thus provides an improved process for releasing an organic acid, preferably a carboxylic, sulphonic or phosphonic acid, especially an alpha-hydroxycarboxylic acid or beta-hydroxycarboxylic acid, from the ammonium salt thereof by release and removal of ammonia and simultaneous extraction of the acid released with a suitable extractant from the aqueous phase. This process corresponds to a reactive extraction. The reactive extraction of an organic acid from the aqueous ammonium salt solution thereof can be improved significantly by the use of a stripping medium or entraining gas, for example nitrogen, air, steam or inert gases, for example argon. The ammonia released is removed from the aqueous solution by the continuous gas stream and can be fed back into a production process. The free acid can be obtained from the extractant by a process such as distillation, rectification, crystallization, re-extraction, chromatography, adsorption, or by a membrane process.

Polymorphic clopidogrel hydrogenesulphate form

Novel orthorombic polymorph of clopidogrel hydrogen sulfate or hydrogen sulfate of methyl (+)-(S)-α-(2-chlorophenyl)-4,5,6,7-tetrahydrothieno[3,2-c]pyridine-5-acetate and a process for its preparation.

Dibenzonaphthyrones

Dibenzonaphthyrone of formula (I) wherein A1and A2independently of each other are unsubstituted or mono- to tetra-substituted o-C6-C18arylene, with the proviso that formula (I) does not represent a dibenzonaphthyrone of the formula The invention further relates to processes for the preparation thereof, to the use thereof for colouring/pigmenting high-molecular-weight organic material and to substance compositions comprising dibenzonaphthyrones.

Resolution of Racemic Carboxylic and Sulfonic Acids via D-Xylose Derived New Cyclic Carbamate Reagents (Oxazolidin-2-ones)

Two new chiral oxazolidin-2-ones have been easily prepared from D-xylose and studied as chiral derivatizing agents (CDA's) for the resolution of racemic carboxylic and sulfonic acids.The resultant diastereomers are readily separated by chromatographic methods and easily hydrolyzed to isolate the resolved materials in high optical purities and to return the CDA's for reuse.

Process for the preparation of D(-)αphenylglycine

The invention provides a process for the preparation of D(-)αphenylglycine by resolution of DLαphenylglycine by means of D(+)camphorsulfonic acid. The present process enables the preparation of D(-)αphenylglycine at a minimum loss of the very expensive starting materials, such as DLαphenylglycine and D(+)camphorsulfonic acid. The salts produced in this process are precipitated from the resolution filtrate and the filtrate may be discarded as effluent water without any danger to the environment.