17026-42-5

Basic information

• Product Name: (+)-Dibenzoyl-D-tartaric acid
• Synonyms: (+)-2,3-DIBENZOYL-D-TARTARIC ACID;(2S,3S)-(+)-DI-O-BENZOYLTARTARIC ACID;(2S,3S)-(+)-DIBENZOYL-D-TARTARIC ACID;(2S,3S)-2,3-BIS-BENZOYLOXY-SUCCINIC ACID;DI-O-BENZOYL-D-TARTARIC ACID;(+)-DIBENZOYL-D-TARTARIC ACID;DIBENZOYL-D-TARTARIC ACID;DIBENZOYL D-TATARIC ACID
• CAS NO: 17026-42-5
• Molecular Formula: C₁₈H₁₄O₈
• Molecular Weight: 358.3
• EINECS: 241-097-1
• Product Categories: Pharmaceutical Intermediates;FINE Chemical & INTERMEDIATES;Chiral Compounds;Substrates;chiral;CHIRAL CHEMICALS;Hydroxy Acids & Deriv.;Chiral Compound;Aromatics;Chiral Reagents;Miscellaneous Reagents
• Mol File: 17026-42-5.mol
• Article Data: 12

Chemical Properties

• Melting Point: 154-156 °C(lit.)
• Boiling Point: 450.75°C (rough estimate)
• Flash Point: 221.8 ºC
• Appearance: White to yellow/Powder
• Density: 1.3806 (rough estimate)
• Refractive Index: 1.5500 (estimate)
• Storage Temp.: Refrigerator
• Solubility: Acetonitrile (Slightly), Ethanol (Slightly), Methanol (Slightly)
• PKA: 1.85±0.25(Predicted)
• Water Solubility: insoluble
• Sensitive: Hygroscopic
• BRN: 2227343
• CAS DataBase Reference: (+)-Dibenzoyl-D-tartaric acid(CAS DataBase Reference)
• NIST Chemistry Reference: (+)-Dibenzoyl-D-tartaric acid(17026-42-5)
• EPA Substance Registry System: (+)-Dibenzoyl-D-tartaric acid(17026-42-5)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• TSCA: Yes
• Hazardous Substances Data: 17026-42-5(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

Different sources of media describe the Uses of 17026-42-5 differently. You can refer to the following data:
1. (+)-Dibenzoyl-D-tartaric acid is a reagent used to produce chiral salts.
2. For chiral resolution(+)-Dibenzoyl-D-tartaric acid is used as a reagent in the preparation of chiral salts. It also serves as a reagent for chiral resolution of amino compounds.

General Description

(+)-2,3-Dibenzoyl-D-tartaric acid is commonly used as an optically active resolving agent in the chiral resolution process such as diastereomeric salt resolution technique.

InChI:InChI=1/C18H14O8/c19-13(11-7-3-1-4-8-11)17(25,15(21)22)18(26,16(23)24)14(20)12-9-5-2-6-10-12/h1-10,25-26H,(H,21,22)(H,23,24)/t17-,18-/m0/s1

Synthetic route

L-1-phenyl-2-(1-pyrrolidinyl)-1-propanone-(-)-dibenzoyl-L-tartaric acid salt → (SR)-(+/-)-1-phenyl-2-(1-pyrrolidinyl)-1-propanone (19134-50-0) + O,O'-dibenzoyl-D-tartaric acid (17026-42-5)

Conditions	Yield
With hydrogenchloride; sodium hydroxide In water; ethyl acetate at 80℃; for 5h; pH=2 - 11.5;	A 87.6% B n/a

S-nicotine dibenzoyl-d-tartrate → O,O'-dibenzoyl-D-tartaric acid (17026-42-5) + nicotin (54-11-5)

Conditions	Yield
With hydrogenchloride In water for 0.166667h; Product distribution / selectivity;	A n/a B 65.5%

D-tartaric acid (147-71-7) + benzoyl chloride (98-88-4) → O,O'-dibenzoyl-D-tartaric acid (17026-42-5)

(+/-)-2,3-O-dibenzoyltartaric acid (2743-38-6, 17026-42-5, 22333-70-6, 100632-52-8, 111955-48-7) → O,O'-dibenzoyl-D-tartaric acid (17026-42-5)

di-O-benzoyl-Dg-tartaric acid-anhydride → O,O'-dibenzoyl-D-tartaric acid (17026-42-5)

Conditions	Yield
With water

(+/-)-2,3-O-dibenzoyltartaric acid (2743-38-6, 17026-42-5, 22333-70-6, 100632-52-8, 111955-48-7) → O,O'-dibenzoyl-D-tartaric acid (17026-42-5) + O,O'-dibenzoyl-L-tartaric acid (2743-38-6)

Conditions	Yield
With N-isopropylcarbamoyl-derivatized cyclofructan-6 column In methanol; acetic acid; triethylamine; acetonitrile at 20℃; Resolution of racemate;

rac-tartaric acid dibenzoate (2743-38-6, 17026-42-5, 22333-70-6, 100632-52-8, 111955-48-7) → O,O'-dibenzoyl-D-tartaric acid (17026-42-5) + O,O'-dibenzoyl-L-tartaric acid (2743-38-6)

Conditions	Yield
With chiral stationary phase including (R)-naphthylethyl-carbamate-functionalized CF6 In methanol; acetic acid; triethylamine; acetonitrile at 20℃; Purification / work up; Resolution of racemate;
With (3R,7R)-1,9-dimethyl-3,7-diphenyl-2,3,5,7,8,9-hexahydro-1H-diimidazo[1,2-c:2',1'-f][1,3,2]diazaphosphinin-4-ium-5-olate-5-oxide In chloroform-d1 at 23℃; Resolution of racemate;

tapentadol (175591-23-8) + O,O'-dibenzoyl-D-tartaric acid (17026-42-5) → (1R,2R)-3-(3-dimethylamino-1-ethyl-2-methylpropyl)phenol hemi-(2S,3S)-dibenzoyltartrate

Conditions	Yield
In acetone at 20℃; for 3h;	100%

O,O'-dibenzoyl-D-tartaric acid (17026-42-5) + 2-phenyl-2-(piperidin-2-yl)acetic acid → d-threo-ritalinic acid dibenzoyl-D-tartrate

Conditions	Yield
Stage #1: 2-phenyl-2-(piperidin-2-yl)acetic acid With oxalic acid In methanol; water at 25 - 30℃; for 1h; Stage #2: O,O'-dibenzoyl-D-tartaric acid In methanol; water at 5 - 70℃; for 10h;	100%

ethyloxirane (106-88-7) + dimethylsulfide (75-18-3) + O,O'-dibenzoyl-D-tartaric acid (17026-42-5) → dimethyl 2-hydroxybutyl sulfonium dibenzoyltartrate (140427-67-4)

Conditions	Yield
In dichloromethane for 24h; Ambient temperature;	99%

N,N'-bis(1,3-dimethyl-2-imidazolidinylidene)-o-benzenediamine + O,O'-dibenzoyl-D-tartaric acid (17026-42-5) → C16H24N6*2C18H14O8

Conditions	Yield
In water; ethyl acetate at 20℃; for 3h;	97.9%

(R)-5-((E)-2-pyrrolidin-3-ylvinyl)pyrimidine (753015-44-0) + O,O'-dibenzoyl-D-tartaric acid (17026-42-5) → (R)-5-((E)-2-pyrrolidin-3-ylvinyl)pyrimidine hemi-di-benzoyl-D-tartarate

Conditions	Yield
In ethanol at 20℃; Reflux;	95.2%
In ethanol Reflux;	95.2%

dimethylsulfide (75-18-3) + O,O'-dibenzoyl-D-tartaric acid (17026-42-5) + oxiranyl-methanol (556-52-5) → 2,3-dihydroxypropyl dimethyl sulfonium dibenzoyltartrate (140630-30-4)

Conditions	Yield
In dichloromethane for 16h; Ambient temperature;	95%

O,O'-dibenzoyl-D-tartaric acid (17026-42-5) + 2-(1-azabicyclo[2.2.2]oct-2-yl)-6-(3-methyl-1H-pyrazol-4-yl)thieno[3,2-d]pyrimidin-4(3H)-one → (2S,3S)-2,3-bis(benzoyloxy)butanedioic acid 2-[1-azabicyclo[2.2.2]oct-2-yl]-6-(3-methyl-1H-pyrazol-4-yl)thieno[3,2-d]pyrimidin-4(3H)-one + (2S,3S)-2,3-bis(benzoyloxy)butanedioic acid 2-[(2S)-1-azabicyclo[2.2.2]oct-2-yl]-6-(3-methyl-1H-pyrazol-4-yl)thieno[3,2-d]pyrimidin-4(3H)-one

Conditions	Yield
In acetic acid; butan-1-ol at 80 - 90℃; for 3h; Solvent; Temperature; Large scale;	A n/a B 94.8%

dimethylsulfide (75-18-3) + hexadecanoic acid, glycidyl ester (7501-44-2) + O,O'-dibenzoyl-D-tartaric acid (17026-42-5) → dimethyl (3-hexadecanoyloxy-2-hydroxypropyl) sulfonium dibenzoyltartrate (140427-55-0)

Conditions	Yield
In dichloromethane for 24h; Ambient temperature;	93%

(R)-5-((E)-2-pyrrolidin-3-ylvinyl)pyrimidine (753015-44-0) + O,O'-dibenzoyl-D-tartaric acid (17026-42-5) → (R)-5-((E)-2-pyrrolidin-3-ylvinyl)pyrimidine mono-di-benzoyl-D-tartarate (1228391-42-1)

Conditions	Yield
In ethanol at 20℃; Heating;	93%
In ethanol Heating;	93%

thiophene (110-01-0) + ethyloxirane (106-88-7) + O,O'-dibenzoyl-D-tartaric acid (17026-42-5) → 2-(2-hydroxybutyl)thiolanium dibenzoyltartrate (140427-51-6)

Conditions	Yield
In dichloromethane for 24h; Ambient temperature;	92%

6-phenethyl-octahydro-pyrrolo[2,3-c]pyridine (1221278-64-3) + O,O'-dibenzoyl-D-tartaric acid (17026-42-5) → C15H22N2*C18H14O8

Conditions	Yield
In ethanol; isopropyl alcohol; toluene at 20℃; for 15h; Resolution of racemate;	92%

O,O'-dibenzoyl-D-tartaric acid (17026-42-5) + 6-phenethyloctahydropyrrolo[2,3-c]pyridine → C15H22N2*C18H14O8 + C15H22N2

Conditions	Yield
In ethanol; isopropyl alcohol; toluene at 20℃; for 16h; Inert atmosphere;	A 92% B n/a

O,O'-dibenzoyl-D-tartaric acid (17026-42-5) + (2RS,3S)-2-amino-3-methylpentanoic acid → C18H14O8*C6H13NO2 + (2S,3S)-2,3-Bis-benzoyloxy-succinic acid; compound with (2R,3S)-2-amino-3-methyl-pentanoic acid

Conditions	Yield
With salicylaldehyde; acetic acid In n-heptane; acetic acid butyl ester at 80℃; for 5h;	A n/a B 90%

O,O'-dibenzoyl-D-tartaric acid (17026-42-5) + zopiclon (43200-80-2) → (R)-6-(5-chloropyridin-2-yl)-7-oxo-6,7-dihydro-5H-pyrrolo[3,4b]pyrazin-5-yl 4-methylpiperazine-1-carboxylate D-(+)-O,O'-dibenzoyltartaric acid salt (144025-94-5) + eszopiclone dibenzoyl-D-tartrate (144025-93-4)

Conditions	Yield
In acetonitrile at 21℃; for 2h; Temperature; Solvent; Optical yield = 87.4 %ee;	A 89.8% B n/a
In 1-methyl-pyrrolidin-2-one; water at 60 - 65℃; for 1h; Resolution of racemate;	A n/a B 86.25%
In dichloromethane at 20℃; for 3h; Purification / work up; Resolution of racemate;
In acetonitrile at 25 - 35℃; for 6 - 7h;
In water; acetonitrile at 25 - 80℃; for 3 - 4.5h; Purification / work up; Resolution of racemate;

(S)-3-(4-chlorophenyl-2-chloropyrid-3-ylmethoxy)azetidine (1186316-72-2) + O,O'-dibenzoyl-D-tartaric acid (17026-42-5) → (S)-3-(4-chlorophenyl-2-chloropyrid-3-ylmethoxy)azetidine dibenzoyl tartate (1186316-77-7)

Conditions	Yield
In isopropyl alcohol	89%

O,O'-dibenzoyl-D-tartaric acid (17026-42-5) + meso-mono(β-o-aminophenyl)triphenylporphyrin (69082-94-6) → C106H72N10O6

Conditions	Yield
Stage #1: O,O'-dibenzoyl-D-tartaric acid With thionyl chloride for 10h; Schlenk technique; Inert atmosphere; Reflux; Stage #2: meso-mono(β-o-aminophenyl)triphenylporphyrin With triethylamine In dichloromethane at 20℃; for 8h;	89%

(±)-erythro/threo-2-phenyl-2-(piperidin-2-yl)acetamide (19395-39-2) + O,O'-dibenzoyl-D-tartaric acid (17026-42-5) → d-threo-[R(R*,R*)]-2-phenyl-2-piperidine-2-yl acetamide dibenzoyl-d-tartrate (741272-48-0)

Conditions	Yield
In isopropyl alcohol at 20 - 55℃; for 6.5h; Resolution of racemate;	88%

(+/-)-2-iodo-6H,12H,5,11-methanodibenzo[b,f][1,5]diazocine (951760-12-6) + O,O'-dibenzoyl-D-tartaric acid (17026-42-5) → (+)-S,S-2-iodo-6,12-dihydro-5,11-methanodibenzo[b,f ][1,5]-diazocine*(+)-O,O′-dibenzoyl-D-tartaric acid (1478192-94-7)

Conditions	Yield
In 1,2-dichloro-ethane at 55 - 60℃; for 120h; Resolution of racemate;	88%

O,O'-dibenzoyl-D-tartaric acid (17026-42-5) + 2,8-dibromo-6H,12H-5,11-methanodibenzo[b,f][1,5]-diazocine (390357-42-3, 1042268-76-7, 1042269-05-5) → (+)-S,S-2,8-dibromo-6,12-dihydro-5,11-methanodibenzo-[b,f ][1,5]diazocine*(+)-O,O′-dibenzoyl-D-tartaric acid (1478192-77-6)

Conditions	Yield
In 1,2-dichloro-ethane at 55 - 60℃; for 120h; Resolution of racemate;	88%

O,O'-dibenzoyl-D-tartaric acid (17026-42-5) + zopiclon (43200-80-2) → D(+)-O,O-dibenzoyl tartarate of zopiclone (1020156-02-8)

Conditions	Yield
In water; acetonitrile at 25 - 35℃; for 7h;	86.63%

2-amino-3,3-dimethylbutanoic acid (33105-81-6) + O,O'-dibenzoyl-D-tartaric acid (17026-42-5) → D-tert-leucine (26782-71-8) + L-tert-leucine dibenzoyl-D-tartrate

Conditions	Yield
In water at 28℃; for 24h; Resolution of racemate;	A 85% B n/a

O,O'-dibenzoyl-D-tartaric acid (17026-42-5) + amfepramone (90-84-6, 39648-49-2, 39648-50-5) → C18H14O8*C13H19NO

Conditions	Yield
With sodium hydroxide In water; acetone at 20℃;	85%

O,O'-dibenzoyl-D-tartaric acid (17026-42-5) + C19H24O4S → C12H20N2O*C18H14O8

Conditions	Yield
Stage #1: C19H24O4S With hydrazine hydrate In ethanol at 65℃; for 16h; Inert atmosphere; Autoclave; Stage #2: O,O'-dibenzoyl-D-tartaric acid In tert-butyl methyl ether for 3.5h;	85%

O,O'-dibenzoyl-D-tartaric acid (17026-42-5) + Benzylidene-methyl-naphthalen-1-yl-phenyl-λ5-phosphane (19432-37-2) → (2S,3S)-2,3-Bis-benzoyloxy-3-carboxy-propionatebenzyl-methyl-naphthalen-1-yl-phenyl-phosphonium; (84673-94-9)

Conditions	Yield
In tetrahydrofuran	84%

O,O'-dibenzoyl-D-tartaric acid (17026-42-5) + trans-2,5-diallylpyrrolidine → bis(trans-2,5-diallylpyrrolidine-1-ium) dibenzoyltartrate (2-)

Conditions	Yield
In chloroform for 32h; Acylation;	84%

O,O'-dibenzoyl-D-tartaric acid (17026-42-5) → (3S,4S)-2,5-dioxotetrahydrofuran-3,4-diyl dibenzoate (17637-11-5, 64339-95-3, 111955-47-6, 116780-73-5)

Conditions	Yield
With acetic anhydride at 85℃; for 2h;	84%
With acetic anhydride at 85℃; for 2h;	84%
With acetic anhydride at 85℃; for 2h;	84%

Upstream product

• 17637-11-5 (+/-)-O,O'-dibenzoyltartaric anhydride 
• 2743-38-6 rac-tartaric acid dibenzoate 
• 2743-38-6 (+/-)-2,3-O-dibenzoyltartaric acid 
• 147-71-7 D-tartaric acid 
• 98-88-4 benzoyl chloride 
• 87-69-4 L-Tartaric acid 

Downstream Products

• 140427-67-4 dimethyl 2-hydroxybutyl sulfonium dibenzoyltartrate 
• 140427-53-8 2-hydroxybutyl methyl phenyl sulfonium dibenzoyltartrate 
• 131101-16-1 (2S,3S)-2,3-Bis-benzoyloxy-succinic acid; compound with (S)-3-(2-amino-ethyl)-5-methoxy-1,3-dimethyl-1,3-dihydro-indol-2-one 
• 140630-10-0 dimethyl (2-hydroxy-3-octadecyloxypropyl) sulfonium dibenzoyltartrate 
• 17637-11-5 (3S,4S)-2,5-dioxotetrahydrofuran-3,4-diyl dibenzoate 
• 192449-16-4 C₁₈H₁₄O₈*C₂₈H₂₈O₂P₂ 
• 1161025-56-4 (R)-5-(2-aminopropyl)-2-methoxybenzenesulfonamide dibenzoyl-D-tartrate 

Relevant articles and documents

Preparation method of (1R,2S)-1-phenyl-2-(1-pyrrolidyl)-1-propanol

The invention discloses a preparation method of (1R,2S)-1-phenyl-2-(1-pyrrolidyl)-1-propanol. According to the preparation method, DL-1-phenyl-2-(1-pyrrolidyl)-1-acetone is taken as a starting material and subjected to resolution, racemization and reduction, and (1R,2S)-1-phenyl-2-(1-pyrrolidyl)-1-propanol is prepared. The yield of one-time resolution is higher than 35%, a resolving agent is easy to recover, and the recovery rate is higher than 90%; the racemization process is performed under the slightly alkaline condition, and the racemization yield is higher; the yield of (1R,2S)-1-phenyl-2-(1-pyrrolidyl)-1-propanol obtained through reduction is higher than 85%. The preparation method has the advantages of mild reaction conditions, stable process, high product optical purity, low cost, high production safety and the like.

PROCESS FOR THE RESOLUTION OF (R,S)-NICOTINE

(R,S)-Nicotine was resolved through diastereomeric salt formation using dibenzoyl-d-tartaric acid and dibenzoyl-l-tartaric acid to obtain enantiomerically pure (S)-nicotine and (R)-nicotine.

Development of new HPLC chiral stationary phases based on native and derivatized cyclofructans

An unusual class of chiral selectors, cyclofructans, is introduced for the first time as bonded chiral stationary phases. Compared to native cyclofructans (CFs), which have rather limited capabilities as chiral selectors, aliphatic-and aromatic-functionalized CF6s possess unique and very different enantiomeric selectivities. Indeed, they are shown to separate a very broad range of racemic compounds. In particular, aliphatic-derivatized CF6s with a low substitution degree baseline separate all tested chiral primary amines. It appears that partial derivatization on the CF6 molecule disrupts the molecular internal hydrogen bonding, thereby making the core of the molecule more accessible. In contrast, highly aromaticfunctionalized CF6 stationary phases lose most of the enantioselective capabilities toward primary amines, however they gain broad selectivity for most other types of analytes. This class of stationary phases also demonstrates high "loadability" and therefore has great potential for preparative separations. The variations in enantiomeric selectivity often can be correlated with distinct structural features of the selector. The separations occur predominantly in the presence of organic solvents.