32634-68-7

Usage

Uses

Used in Pharmaceutical Industry:
2,3-Di-O-para-toluoyl-D-tartaric acid is used as an inhibitor of enzymes, particularly for Rivastigmine USP Related Compound A. Its chemical structure allows it to interact with specific enzymes, thereby inhibiting their activity and contributing to the development of pharmaceutical products.
Used in Medical Applications:
In the medical field, 2,3-Di-O-para-toluoyl-D-tartaric acid is utilized as a blood volume expander. Its properties enable it to increase the volume of blood, which can be beneficial in treating conditions where blood volume needs to be maintained or increased.
Used in Chemical Synthesis:
Due to its unique chemical structure, 2,3-Di-O-para-toluoyl-D-tartaric acid can be used as a starting material or intermediate in the synthesis of various chemical compounds. Its reactivity and functional groups make it a valuable component in the development of new molecules with potential applications in different industries.

Flammability and Explosibility

Notclassified

InChI:InChI=1/C18H18O6/c1-11-3-7-13(8-4-11)23-15(17(19)20)16(18(21)22)24-14-9-5-12(2)6-10-14/h3-10,15-16H,1-2H3,(H,19,20)(H,21,22)

Synthetic route

rac-O,O'-di-p-toluoyltartaric acid (32634-66-5, 32634-68-7, 100168-11-4, 104528-81-6) → (2S,3S)-di-4-toluoyltartaric acid (32634-68-7)

Conditions	Yield
ueber das Cinchonin-Salz;

di-O-p-toluoyl-Dg-tartaric acid-anhydride → (2S,3S)-di-4-toluoyltartaric acid (32634-68-7)

Conditions	Yield
With water; acetone

(R)-2-cyclopropylaminocyclohexanol di-p-toluoyl-D-tartrate (339546-21-3) → (R)-2-cyclopropylaminocyclohexanol (339546-20-2) + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7)

Conditions	Yield
With sodium hydroxide In water at 20 - 30℃; for 1h; Product distribution / selectivity;	A n/a B n/a

(+)-di-O,O'-toluoyl-D-tartaric acid mono-NH4 salt → (2S,3S)-di-4-toluoyltartaric acid (32634-68-7)

Conditions	Yield
With Amberlite 1R In isopropyl alcohol Product distribution / selectivity;
With hydrogenchloride In dichloromethane; water pH=< 0.5; Product distribution / selectivity;

(3S,4S)-2,5-dioxotetrahydrofuran-3,4-diyl bis(4-methylbenzoate) (72842-25-2) → (2S,3S)-di-4-toluoyltartaric acid (32634-68-7)

Conditions	Yield
With water In toluene for 5h; Reflux; Large scale;	374.4g

rac-O,O'-di-p-toluoyltartaric acid (32634-66-5, 32634-68-7, 100168-11-4, 104528-81-6) → Di-p-toluoyl-L-tartaric acid (32634-66-5) + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7)

Conditions	Yield
With C22H24N2(2+)*2CF3O3S(1-) In aq. acetate buffer at 20℃; pH=8.1; Resolution of racemate;

(2S,3S)-di-4-toluoyltartaric acid (32634-68-7) + (R,S)-3-iso-butyl-4-aminobutyric acid (128013-69-4, 130912-52-6, 148553-50-8, 148553-51-9) → (S)-pregabalin O,O'-di-p-toluoyl-(D)-tartrate + (R)-pregabalin O,O'-di-p-toluoyl-(D)-tartrate

Conditions	Yield
In water; butan-1-ol at 20 - 25℃; Resolution of racemate;	A 98% B n/a

(R)-5-((E)-2-pyrrolidin-3-ylvinyl)pyrimidine (753015-44-0) + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7) → (R)-5-((E)-2-pyrrolidin-3-ylvinyl)pyrimidine mono-di-p-toluoyl-D-tartarate (1228391-41-0)

Conditions	Yield
In ethanol Reflux;	96.1%
In ethanol Reflux;	96.1%

rac-trans-2-methylamino-cyclohexanol (20431-81-6) + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7) → 2C7H15NO*C20H18O8 + trans-2-(methylamino)cyclohexanol (21651-84-3)

Conditions	Yield
In ethanol at 45 - 60℃; for 1h;	A 95% B n/a

7-trifluoromethyl-2,3,4,5-tetrahydro-1,5-methylene-1H-3-benzazepine + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7) → (1S,8R)-(+)-4-trifluoromethyl-10-azatricyclo[6.3.1.0(2,7)]dodeca-2(7),3,5-triene di-p-toluoyl-D-(-)-tartaric acid salt (873788-21-7)

Conditions	Yield
In acetonitrile at 82℃; for 1 - 24h; Product distribution / selectivity;	94%

(2S,3S)-di-4-toluoyltartaric acid (32634-68-7) + (4aS,8aS)-rel-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-one (510-77-0, 1668-86-6, 7318-55-0) → [(-)-narwedine][di-p-toluoyl-D-tartrate]

Conditions	Yield
In ethanol at 40℃; Heating / reflux;	90%

(2S,3S)-di-4-toluoyltartaric acid (32634-68-7) + 2-(tert-butylamino)-1-(2,2-dimethyl-4H-benzo[d][1,3]dioxan-6-yl)ethanol (54208-72-9) → 2C16H25NO3*C20H18O8

Conditions	Yield
In methanol for 0.166667h; Heating / reflux;	90%
In methanol for 0.25h; Heating / reflux;	73%

2-(1-aminoethyl)-N-(5-chloro-4-(trifluoromethyl)pyridin-2-yl)thiazole-5-carboxamide (1095823-56-5) + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7) → C12H10ClF3N4OS (1095825-44-7) + C12H10ClF3N4OS*C20H18O8 (1095823-60-1)

Conditions	Yield
In water; isopropyl alcohol at 45 - 53℃; for 21h; Purification / work up; Resolution of racemate;	A n/a B 88%

(8-hydroxy-4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-yl)acetonitrile + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7) → 2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylaminedi-p-toluoyl-L-(-)-tartrate

Conditions	Yield
Stage #1: (8-hydroxy-4,5-dibromo-1,2,6,7-tetrahydro-8H-indeno[5,4-b]furan-8-yl)acetonitrile With ammonia; hydrogen In ethanol at 55℃; under 18751.9 Torr; for 15h; Stage #2: (2S,3S)-di-4-toluoyltartaric acid at 20℃; for 0.75h; Temperature; Pressure; Solvent;	87.8%

(2S,3S)-di-4-toluoyltartaric acid (32634-68-7) + lofexidine hydrochloride (21498-08-8) → (+/-)-lofexidine di-p-toluoyl-D-tartarate + (+/+)-lofexidine di-p-toluoyl-D-tartarate

Conditions	Yield
In ethanol	A 87% B n/a

(2S,3S)-di-4-toluoyltartaric acid (32634-68-7) + (S)-1-(2-piperidino-phenyl)-3-methyl-1-butylamine (108157-52-4) → (S)-3-methyl-1-(2-piperidino-phenyl)-1-butylamine di-p-toluoyl-D-tartaric acid salt (1098066-89-7)

Conditions	Yield
With toluene-4-sulfonic acid In methanol; water at 25 - 60℃; Product distribution / selectivity;	85.7%

(2S,3S)-di-4-toluoyltartaric acid (32634-68-7) + (4aS,8aS)-rel-3-methoxy-11-methyl-4a,5,9,10,11,12-hexahydro-6H-benzo[2,3]benzofuro[4,3-cd]azepin-6-one (510-77-0, 1668-86-6, 7318-55-0) → [(-)-narwedine]2[di-p-toluoyl-D-tartrate]

Conditions	Yield
In ethanol at 20 - 40℃; for 19h; Heating / reflux;	83%
In ethanol at 40℃; Heating / reflux;	79%

5-azaspiro[2.4]heptane-6-carboxylic acid + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7) → (S)-5-azaspiro[2.4]heptane-6-carboxylic acid D-di-p-methylbenzoyltartrate

Conditions	Yield
Stage #1: 5-azaspiro[2.4]heptane-6-carboxylic acid; (2S,3S)-di-4-toluoyltartaric acid With acetic acid at 60℃; for 0.333333h; Stage #2: With ethyl acetate at 50℃; for 1.5h; Enzymatic reaction; Stage #3: With salicylaldehyde at 50℃; for 18h;	83%

1-Benzyl-3-methyl-4-piperidon (34737-89-8) + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7) → (R)-1-benzyl-3-methylpiperidin-4-one (2S,3S)-2,3-bis((4-methylbenzoyl)oxy)succinic acid salt

Conditions	Yield
In acetonitrile at 40℃; for 12h; Large scale;	83%
In acetonitrile at 40℃; for 12h; Large scale;	83%
In acetonitrile at 40℃; for 12h; Large scale;	83%

(S)-methyl 2-(8-fluoro-3-(2-methoxy-5-(trifluoromethyl)phenyl)-2-(4-(3-methoxyphenyl)piperazin-1-yl)-3,4-dihydroquinazolin-4-yl)acetate + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7) + ethyl acetate (141-78-6) → (S)-methyl 2-(8-fluoro-3-(2-methoxy-5-(trifluoromethyl)phenyl)-2-(4-(3-methoxyphenyl)piperazin-1-yl)-3,4-dihydroquinazolin-4-yl)acetate (2S,3S)-2,3-bis((4-methylbenzoyl)oxy)succinate ethyl acetate

Conditions	Yield
In toluene at 45℃; Inert atmosphere;	82%

(2S,3S)-di-4-toluoyltartaric acid (32634-68-7) → (+)-(S,S)-D-O,O'-di-p-toluoyltartaric acid monosodium salt

Conditions	Yield
With sodium hydroxide In water for 0.166667h; Sonication;	82%

(2S,3S)-di-4-toluoyltartaric acid (32634-68-7) + [2R-[2α(R*),3α]]-2-[1-[3,5-bis(trifluoromethyl)phenyl]ethoxy]-3-(4-fluorophenyl)morpholine (171338-27-5) → BFM2-(D)-DTTA (1404074-27-6)

Conditions	Yield
In isopropyl alcohol at 50 - 55℃; for 0.333333h; Product distribution / selectivity; Industry scale;	80%

didesmethylcitalopram (62498-69-5) + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7) → S-(+)-1-(3-amino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile (-)-di-p-toluoyltartrate + R-1-(3-amino-propyl)-1-(4-fluoro-phenyl)-1,3-dihydro-isobenzofuran-5-carbonitrile (-)-di-p-toluoyltartrate

Conditions	Yield
Stage #1: didesmethylcitalopram; (2S,3S)-di-4-toluoyltartaric acid In acetonitrile at 20℃; Stage #2: In water; acetonitrile at 0 - 60℃; Solvent;	A 80% B n/a

(2S,3S)-di-4-toluoyltartaric acid (32634-68-7) + (R)-(+)-N,α-dimethylbenzylamine (5933-40-4) → (R)-N-methyl-α-methylbenzylammonium di-p-toluoyl-D-tartrate

Conditions	Yield
In methanol; ethyl acetate at 20℃; for 1h;	80%

N-methyl-N-[(S)-1-phenylethyl]amine (19131-99-8) + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7) → (S)-N-methyl-α-methylbenzylammonium di-p-toluoyl-D-tartrate

Conditions	Yield
In methanol; ethyl acetate at 20℃; for 1h;	80%

α-methyl-N-[3-[3-(trifluoromethyl)phenyl]propyl]-1-naphthalenemethanamine (1025064-33-8) + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7) → (R)-cinacalcet (-)-di-para-D-toluoyl tartrate

Conditions	Yield
In ethyl acetate at 25 - 65℃; for 0.75h;	78%

C30H30F4N4O4*C7H6O3 + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7) → (2S,3S)-2,3-bis[(4-methylbenzoyl)oxy]succinic acid {(4S)-8-fluoro-2-[4-(3-methoxyphenyl)piperazin-1-yl]-3-(2-methoxy-5-(trifluormethyl)phenyl)-3,4-dihydroquinazolin-4-yl}acetic acid methyl ester (917389-30-1)

Conditions

Yield

Stage #1: C30H30F4N4O4*C7H6O3 With potassium phosphate In water; toluene at 20℃; for 1h; Stage #2: With potassium phosphate; (1S,2S,4S,5R)-1-(3,5-bis(trifluoromethyl)benzyl)-2-((R)-hydroxy(1-(3-(trifluoromethyl)benzyl)quinolin-1-ium-4-yl)methyl)-5-vinylquinuclidin-1-ium bromide In water; N,N-dimethyl-formamide; toluene at 0℃; Stage #3: (2S,3S)-di-4-toluoyltartaric acid In ethyl acetate; toluene at 20℃; for 12h;

78%

amfepramone (90-84-6, 39648-49-2, 39648-50-5) + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7) → C20H18O8*C13H19NO

Conditions	Yield
With sodium hydroxide In water; acetone at 20℃;	78%

C15H18N2O2 + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7) → C20H18O8*C15H18N2O2

Conditions	Yield
In water; acetonitrile Solvent;	78%

trans-N-(2-hydroxycyclohexyl)-N-cyclopropylamine (726201-98-5) + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7) → (R)-2-cyclopropylaminocyclohexanol di-p-toluoyl-D-tartrate (339546-21-3)

Conditions	Yield
With hydrogenchloride In methanol; water at 20 - 70℃; for 2.5h; Resolution of racemate;	77.8%

rac-7-(3-pyridinyl)-1,7-diazaspiro[4.4]nonane (646055-67-6) + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7) → (S)-7-(3-pyridinyl)-1,7-diazaspiro[4.4]nonane mono-(+)-di-O,O'-p-toluoyl-D-tartrate (1174118-94-5)

Conditions	Yield
In ethanol at 20 - 50℃; Purification / work up; Reflux; Resolution of racemate;	76.4%

(±)-2-(pyridin-3-ylmethylidene)-1-azabicyclo[2.2.2]octan-3-one (273748-55-3) + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7) → (2S)-2-((3-pyridinyl)methyl)-1-azabicyclo[2.2.2]octan-3-one di-p-toluoyl-D-tartrate (1111942-08-5)

Conditions	Yield
Stage #1: (±)-2-(pyridin-3-ylmethylidene)-1-azabicyclo[2.2.2]octan-3-one With hydrogen; palladium 10% on activated carbon In methanol at 20℃; for 12h; Industry scale; Stage #2: (2S,3S)-di-4-toluoyltartaric acid In ethanol at 15 - 30℃; for 13h; Industry scale; Heating / reflux;	76.2%

(2S,3S)-di-4-toluoyltartaric acid (32634-68-7) → (3S,4S)-2,5-dioxotetrahydrofuran-3,4-diyl bis(4-methylbenzoate) (72842-25-2)

Conditions	Yield
With acetic anhydride at 85℃; for 2h;	76%

C23H24F3N (1206633-34-2) + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7) → C20H18O8*(x)C23H24F3N

Conditions	Yield
In ethyl acetate at 25 - 65℃; for 0.75h;	74.3%

(2S,3S)-di-4-toluoyltartaric acid (32634-68-7) + 3-amino-5-phenyl-1,3-dihydro-2H-benzo[b]azepin-2-one → (S)-3-amino-5-phenyl-1,3-dihydro-2H-benzo[b]azepin-2-one

Conditions	Yield
Stage #1: (2S,3S)-di-4-toluoyltartaric acid; 3-amino-5-phenyl-1,3-dihydro-2H-benzo[b]azepin-2-one In 1,4-dioxane at 20℃; for 24h; Stage #2: With sodium hydroxide In water at 20℃; for 4h;	73.2%
Stage #1: (2S,3S)-di-4-toluoyltartaric acid; 3-amino-5-phenyl-1,3-dihydro-2H-benzo[b]azepin-2-one In 1,4-dioxane at 20℃; for 24h; Stage #2: With sodium hydroxide at 20℃; for 4h;	73.2%

(-)-(S)-N,N-dimethyl-1-phenylethylamine (17279-31-1) + (2S,3S)-di-4-toluoyltartaric acid (32634-68-7) → (S)-N,N-dimethyl-α-methylbenzylammonium di-p-toluoyl-D-tartrate

Conditions	Yield
In Isopropyl acetate Reflux;	73%

Upstream product

• 32634-66-5 rac-O,O'-di-p-toluoyltartaric acid 
• 72842-25-2 (3S,4S)-2,5-dioxotetrahydrofuran-3,4-diyl bis(4-methylbenzoate) 
• 339546-21-3 (R)-2-cyclopropylaminocyclohexanol di-p-toluoyl-D-tartrate 

Downstream Products

• 68935-25-1 l-nicotine di-(p-toluoyl)-d-tartrate 
• 238762-33-9 2C₁₆H₂₅NO₃*C₂₀H₁₈O₈ 

Relevant academic research and scientific papers

Diquats with Robust Chirality: Facile Resolution, Synthesis of Chiral Dyes, and Application as Selectors in Chiral Analysis

Diquats with extremely high racemization barriers with ΔG≠theor of 233 kJ mol?1 at 180 °C are described. Reported configurational robustness is due to a combination of two structural features: the rigid o-xylylene tether connecting the nitrogen atoms and the presence of two substituents in the bay region of the bipyridinium scaffold. The straightforward synthesis of diquats, plus facile resolution and derivatization make them attractive for chiral application studies. This is demonstrated by: 1) synthesis of the first non-racemic diquat dyes with pronounced chiroptical properties, and 2) capability of diquats to interact stereospecifically with chiral molecules. This suggests potential for diquat derivatives to be used as chiral selectors in separation methods.

A D-P-methyl-dibenzoyl tartaric acid synthesis method (by machine translation)

The invention discloses a Di-p-toluoyl-D-tartaric acid synthetic method. D-Tartaric acid and p-toluoyl chloride are taken as raw materials, copper sulfate is taken as a catalyst, toluene is taken as a solution, Di-p-toluoyl-D-tartaric anhydride is obtained through a reaction, an equivalent amount of water is added, and the toluene is hydrolyzed to obtain Di-p-toluoyl-D-tartaric acid, wherein the toluene solution, and water and the toluene in the hydrolysis can be recycled. The method is simple in process, safe and easy to operate, the process yield reaches over 95 percent; and at the same time, the cost of the raw materials is low, a part of raw material can be recycled, the purity of a finished product is high, and an excellent chiral resolution performance is achieved.

Recovery of optically active tartaric acid resolving agents

A process for the recovery of substituted tartaric acid resolving agents from resolution mother liquors or isolated diastereomeric salts, characterized in that the diastereomeric salt of an enantiamerically enriched amine and the substituted tartaric acid derivative in an organic solvent is treated with a base, extracting said substituted tartaric acid derivative into an aqueous phase, adding an acid to the separated aqueous phase while monitoring the pH-value, precipitating mono salts of substituted tartaric acid derivatives, isolating said mono salts, and liberating the substituted tartaric acid derivative by an acidic treatment.

PROCESSES FOR THE RECOVERY OF OPTICALLY ACTIVE DIACYLTARTATIC ACIDS

When a salt of an amine and an optically active diacyltartaric acid, or a diastereomer salt of an optically active amine and an optically active diacyltartaric acid, obtained by optically resolving a racemic amine using the optically active diacyltartaric acid, is salt-exchanged with an acid aqueous solution, the optically active diacyltartaric acid is added in the acid aqueous solution beforehand. Furthermore, a raw material containing a racemic amine and an optically active diacyltartaric acid is optically resolved, and the diastereomer salt of the optically active amine and the optically active diacyltartaric acid respectively of one isomer type, is separated. The obtained diastereomer salt is dissociated using an acid aqueous solution containing the optically active diacyltartaric acid, for recovering the optically active diacyltartaric acid, and the obtained' optically active diacyltartaric acid is recycled into an optical resolution step as a raw material of the optical resolution step.