(-)-Di-p-toluoyl-L-tartaric acid Chemical Properties

Melting point:

169-171 °C(lit.)

alpha 

-142 º (c=10, EtOH)

Boiling point:

432.57°C (rough estimate)

Density 

1.3084 (rough estimate)

bulk density

500kg/m3

refractive index 

-139 ° (C=1, EtOH)

storage temp. 

Store below +30°C.

solubility 

Chloroform (Slightly), Ethanol (Slightly), Methanol (Slightly)

pka

1.46±0.25(Predicted)

form 

Crystalline Powder

color 

White to yellow

optical activity

[α]20/D 138°, c = 1 in ethanol

Water Solubility 

soluble

BRN 

2022481

CAS DataBase Reference

32634-66-5(CAS DataBase Reference)

EPA Substance Registry System

Butanedioic acid, 2,3-bis[(4-methylbenzoyl)oxy]-, [R-(R*,R*)]- (32634-66-5)

Safety Information

Hazard Codes 

Xi

Risk Statements 

36/37/38

Safety Statements 

22-24/25-36/37-26

WGK Germany 

3

TSCA 

T

HS Code 

29181300

MSDS

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(-)-Di-p-toluoyl-L-tartaric acid Usage And Synthesis

Uses

(-)-di-p-toluoyl-l-tartaric acid can be used as a chiral resolving agent for the resolution of the racemic bases to isolate the (-)-enantiomeric forms.

Chemical Properties

white to light yellow crystal powde

Uses

Escitalopram intermediate

Uses

(-)-O,O’-Di-p-toluoyl-L-tartaric Acid is a useful reagent for the preparation of the upadacitinib salt compound.

Uses

Inhibitor of enzyme

General Description

(-)-O,O′-Di-p-toluoyl-L-tartaric acid is a O,O′-diacyl tartaric acid derivative that can be prepared by the resolution of its racemate in the presence of cinchonine.

Synthesis

The general procedure for the synthesis of di-p-toluoyltartaric acid and compound (CAS: 243640-19-9) from compound (CAS: 869749-09-7) was as follows: (R)-α-(2,3-dimethoxyphenyl)-4-piperidine methanol was mixed with (2R,3R)-(-)-di-(p-toluoyl)tartaric acid salt (7 g) in 10 mL of concentrated ammonia and methanol were stirred well. After 2 hours of reaction, 30 mL of water was added and evaporated to remove methanol and ammonia. Subsequently, another 30 mL of water was added and the precipitate was collected, rinsed with water and dried to give (R)-α-(2,3-dimethoxyphenyl)-4-piperidine methanol (1), which typically has an enantiomeric excess of 85% (ee). After acidification of the aqueous layer with 1N hydrochloric acid, the precipitate was collected and dried to recover (2R,3R)-(-)-di-(p-toluoyl)tartaric acid.

References

[1] Patent: EP1734037, 2006, A2. Location in patent: Page/Page column 53

(-)-Di-p-toluoyl-L-tartaric acid(32634-66-5)Related Product Information

• Hexamethylphosphoramide
• D(-)-Tartaric acid
• Benzoyl peroxide
• (+)-Dibenzoyl-D-tartaric acid
• L(+)-Tartaric acid
• O-Phthalimide
• Calcium folinate
• Dimethyl sulfone
• Folic acid
• Ethyl 2-(Chlorosulfonyl)acetate
• Dibenzoyl-L-tartaric acid
• DL-Tartaric acid
• Glycine
• Tosyl cyanide
• L(+)-Diethyl L-tartrate
• 4-Chloro-3-Pyridine-sulfonyl-chloride
• 4-Hydroxypyridine-3-sulfonic acid
• 4-(Hydroxyamino)-4-oxobutanoic acid