62708-56-9

Basic information

• Product Name: (-)-Dibenzoyl-L-tartaric acid monohydrate
• Synonyms: O,O'-Dibenzoyl-d-Tartaric acid Anhydrous;(-)-O,O''-DIBENZOYL-L-WEINSUREMONOHYDRAT;DIBENZOYL-L-TARARIC ACID MOTOHYDRATE;L-(-)DIBENZOYL-L-TARTARIC ACID 1-HYDRATE;(2S,3S)-2,3-bis(benzoyloxy)succinic acid hydrate;(-)-O,O'-DIBENZOYL-L-TARTARIC ACID HYDRATE;(-)-O,O'-DIBENZOYL-L-TARTARIC ACID MONOHYDRATE;(2R,3R)-(-)-DI-O-BENZOYL-TARTARIC ACID MONOHYDRATE
• CAS NO: 62708-56-9
• Molecular Formula: C₁₈H₁₄O₈*H₂O
• Molecular Weight: 376.31
• EINECS: 220-374-0
• Product Categories: Pharmaceutical Intermediates;FINE Chemical & INTERMEDIATES;chiral;Carboxylic Acids (Chiral);Chiral Building Blocks;for Resolution of Bases;Optical Resolution;Synthetic Organic Chemistry;CHIRAL CHEMICALS;Hydroxy Acids & Deriv.;Chiral Compound;Carboxylic AcidsAsymmetric Synthesis;Chiral Building Blocks;Chiral Resolution Reagents;Chiral Resolving Reagents;Organic Building Blocks;Widely used in chiral especially racemic amine compounds
• Mol File: 62708-56-9.mol
• Article Data: 0

Chemical Properties

• Melting Point: 88-89 °C(lit.)
• Boiling Point: 669.9 °C at 760 mmHg
• Flash Point: 358.9 °C
• Appearance: White/Powder
• Vapor Pressure: 1.45E-15mmHg at 25°C
• Refractive Index: -108.5 ° (C=1, EtOH)
• Storage Temp.: Store below +30°C.
• Water Solubility: SOLUBLE
• BRN: 4065263
• CAS DataBase Reference: (-)-Dibenzoyl-L-tartaric acid monohydrate(CAS DataBase Reference)
• NIST Chemistry Reference: (-)-Dibenzoyl-L-tartaric acid monohydrate(62708-56-9)
• EPA Substance Registry System: (-)-Dibenzoyl-L-tartaric acid monohydrate(62708-56-9)

Safety Data

• Hazard Codes: Xi
• Statements: 36
• Safety Statements: 26-36-37/39
• WGK Germany: 3
• RTECS: WW8070000
• F: 3
• TSCA: Yes
• Hazardous Substances Data: 62708-56-9(Hazardous Substances Data)

Usage

Chemical Properties

white to light yellow crystal powde

Uses

(-)-Dibenzoyl-L-tartaric acid is used as an intermediate in pharmaceutical and agro chemical industries. It is used as chiral auxiliary in organic synthesis and as a resolution agent in the synthesis of rameleton.

General Description

(-)-O,O′-Dibenzoyl-L-tartaric acid monohydrate may be used as a chiral resolving agent for the resolution of racemic bioactive compounds such as (±)-3-(3-hydroxyphenyl)-N-(1-propyl)-piperidine and (±)-2-(5,6-dimethoxy-1,2,3,4-tetrahydro-1-naphthyl)-imidazoline to isolate the corresponding (-)-enantiomeric forms.

Purification Methods

Crystallise the acid from water (18g from 400 mL boiling H2O) and stir vigorously while cooling in order to obtain crystals; otherwise an oil will separate which solidifies on cooling. Dry it in a vacuum desiccator over KOH/H2SO4 (yield 16.4g) as monohydrate, m 88-89o. It crystallises from xylene as the anhydrous acid, m 173o (150-153o). It does not crystallise from *C6H6, toluene, *C6H6/pet ether (oil), or CHCl3/pet ether. [Butler & Cretcher J Am Chem Soc 55 2605 1933, Acs et al. Tetrahedron 41 2465 1985, R(+) Beilstein 9 IV 557, S(-) Beilstein 9 III 870.]

InChI:InChI=1/C18H14O8.H2O/c19-15(20)13(25-17(23)11-7-3-1-4-8-11)14(16(21)22)26-18(24)12-9-5-2-6-10-12;/h1-10,13-14H,(H,19,20)(H,21,22);1H2

Synthetic route

(-)-O,O′-dibenzoyl-L-tartaric acid monohydrate (62708-56-9) + (+/-)-2,8-dichloro-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine → (-)-R,R-2,8-dichloro-6,12-dihydro-5,11-methanodibenzo-[b,f ][1,5]diazocine*(-)-O,O′-dibenzoyl-L-tartaric acid (1478259-27-6)

Conditions	Yield
In 1,2-dichloro-ethane at 55 - 60℃; for 120h; Resolution of racemate;	91%

(+/-)-2-iodo-6H,12H,5,11-methanodibenzo[b,f][1,5]diazocine (951760-12-6) + (-)-O,O′-dibenzoyl-L-tartaric acid monohydrate (62708-56-9) → (-)-R,R-2-iodo-6,12-dihydro-5,11-methanodibenzo[b,f ][1,5]-diazocine*(-)-O,O′-dibenzoyl-L-tartaric acid (1478192-90-3)

Conditions	Yield
In 1,2-dichloro-ethane at 55 - 60℃; for 120h; Resolution of racemate;	90%

(-)-O,O′-dibenzoyl-L-tartaric acid monohydrate (62708-56-9) + 2,8-dibromo-6H,12H-5,11-methanodibenzo[b,f][1,5]-diazocine (390357-42-3, 1042268-76-7, 1042269-05-5) → (-)-R,R-2,8-dibromo-6,12-dihydro-5,11-methanodibenzo-[b,f ][1,5]diazocine*(-)-O,O′-dibenzoyl-L-tartaric acid (1478192-74-3)

Conditions	Yield
In 1,2-dichloro-ethane at 55 - 60℃; for 120h; Resolution of racemate;	89%

2,8-dimethoxy-6H,12H-5,11-methanodibenzo[b,f][1,5]diazocine (847-23-4) + (-)-O,O′-dibenzoyl-L-tartaric acid monohydrate (62708-56-9) → (-)-R,R-2,8-dimethoxy-6,12-dihydro-5,11-methanodibenzo-[b,f ][1,5]diazocine*(-)-O,O′-dibenzoyl-L-tartaric acid (1202533-76-3)

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

ethanol (64-17-5) + (+/-)-crispine A (15889-93-7) + (-)-O,O′-dibenzoyl-L-tartaric acid monohydrate (62708-56-9) → (-)-crispine A*(-)-dibenzoyl-L-tartaric acid*ethanol

Conditions	Yield
Reflux; optical yield given as %de;	81%

(-)-O,O′-dibenzoyl-L-tartaric acid monohydrate (62708-56-9) + (5S,11S)-2,8-diiodo-6,12-dihydro-5,11-methanodibenzo[b,f][1,5]diazocine (390357-41-2, 1042269-07-7, 1042268-78-9) → (-)-R,R-2,8-diiodo-6,12-dihydro-5,11-methanodibenzo[b,f ]-[1,5]diazocine*(-)-O,O′-dibenzoyl-L-tartaric acid (1478192-79-8)

Conditions	Yield
In 1,2-dichloro-ethane at 45 - 50℃; for 120h; Resolution of racemate;	76%

(-)-O,O′-dibenzoyl-L-tartaric acid monohydrate (62708-56-9) + (+/-)-2-bromo-6H,12H,5,11-methanodibenzo[b,f][1,5]diazocine → (-)-R,R-2-bromo-6,12-dihydro-5,11-methanodibenzo[b,f ]-[1,5]diazocine*(-)-O,O′-dibenzoyl-L-tartaric acid (1478192-97-0)

Conditions	Yield
In 1,2-dichloro-ethane at 55 - 60℃; for 120h; Resolution of racemate;	69%

Troeger's base (529-81-7) + (-)-O,O′-dibenzoyl-L-tartaric acid monohydrate (62708-56-9) → (-)-R,R-2,8-dimethyl-6,12-dihydro-5,11-methanodibenzo-[b,f ][1,5]diazocine*(-)-O,O′-dibenzoyl-L-tartaric acid (900804-66-2, 900804-67-3)

Conditions	Yield
In 1,2-dichloro-ethane at 45 - 50℃; for 120h; Resolution of racemate;	66%

FeC10H9CH(C6H5)NH2 + (-)-O,O′-dibenzoyl-L-tartaric acid monohydrate (62708-56-9) → (C5H5)Fe(C5H4CH(C6H5)NH2)*(CHOCOC6H5)2(COOH)2 + (C5H5)Fe(C5H4CH(C6H5)NH2)*(CHOCOC6H5)2(COOH)2

Conditions	Yield
In ethanol hot soln. of acid was added to a hot soln. of amine; R salt was obtained by pptn. on cooling and successive extraction with hot ethanol, S salt was obtained after evapn. of mother liquor;	A 37.5% B 29.1%

(-)-O,O′-dibenzoyl-L-tartaric acid monohydrate (62708-56-9) + water → O-benzoyl-Lg-tartaric acid

(-)-O,O′-dibenzoyl-L-tartaric acid monohydrate (62708-56-9) → (+)-4,5-dihydro-1-phenyl-1,3,4-trimethyl-1H-2,4-benzodiazepine

DL-threo-3-(3,4-methylenedioxyphenyl)serine methyl ester + (-)-O,O′-dibenzoyl-L-tartaric acid monohydrate (62708-56-9) → L-threo-3-(3,4-methylenedioxyphenyl)serine methyl ester · dibenzoyl-L-tartarate

Conditions	Yield
In 1,4-dioxane

tris(2,4-pentanedionato)ruthenium(III) (31378-26-4, 31378-27-5, 14284-93-6) + (-)-O,O′-dibenzoyl-L-tartaric acid monohydrate (62708-56-9) → Λ(+)-tris(pentane-2,5-dionato)ruthenium + (+)275(CD)-tris(2,4-pentanedionato)ruthenium(III) (31378-27-5)

Conditions	Yield
In cyclohexane; benzene racemic Ru complex and a ligand stirring in a solvent mixt. at room temp. for 2 d, solid filtering off and washing with C6H14-C6H6 (2:1) mixt., chloroform adding, extg. with aq. NaHCO3, evapg.; puirified by fractional recrystn. from petroleum ether and CH2Cl2 (2:1), identified by absorption and OPC spectra;

rhodium(III) acetylacetonate + (-)-O,O′-dibenzoyl-L-tartaric acid monohydrate (62708-56-9) → Λ-tris(acetylacetonato)rhodium(III) + Δ-tris(acetylacetonato)rhodium(III)

Conditions	Yield
In cyclohexane; benzene racemic Rh complex and a ligand stirring in a solvent mixt. at room temp. for 2 d, solid filtering off and washing with C6H14-C6H6 (2:1) mixt., chloroform adding, extg. with aq. NaHCO3, evapg.; puirified by fractional recrystn. from petroleum ether and CH2Cl2 (2:1), identified by absorption and OPC spectra;

iridium(III) acetylacetonate + (-)-O,O′-dibenzoyl-L-tartaric acid monohydrate (62708-56-9) → Λ-[Rh(III)(acetylacetonato)3] + Δ-[Rh(III)(acetylacetonato)3]

Conditions	Yield
In cyclohexane; benzene racemic Ru complex and a ligand stirring in a solvent mixt. at room temp. for 2 d, solid filtering off and washing with C6H14-C6H6 (2:1) mixt., chloroform adding, extg. with aq. NaHCO3, evapg.; puirified by fractional recrystn. from petroleum ether and CH2Cl2 (2:1), identified by absorption and OPC spectra;

cobalt(III) acetylacetonate + (-)-O,O′-dibenzoyl-L-tartaric acid monohydrate (62708-56-9) → cobalt(III) acetylacetonate + Δ-tris(acetylacetonato)cobalt(III)

Conditions	Yield
In cyclohexane; benzene racemic Co complex and a ligand stirring in a solvent mixt. at room temp. for 2 d, solid filtering off and washing with C6H14-C6H6 (2:1) mixt., chloroform adding, extg. with aq. NaHCO3, evapg.; puirified by fractional recrystn. from petroleum ether and CH2Cl2 (2:1), identified by absorption and OPC spectra;

chromium(III) acetylacetonate + (-)-O,O′-dibenzoyl-L-tartaric acid monohydrate (62708-56-9) → (-)-Δ-tris(pentane-2,4-dionato)chromium(III) + Λ-(+)-tris(acetylacetonato)chromium(III)

Conditions	Yield
In cyclohexane; benzene racemic Cr complex and a ligand stirring in a solvent mixt. at room temp. for 2 d, solid filtering off and washing with C6H14-C6H6 (2:1) mixt., chloroform adding, extg. with aq. NaHCO3, evapg.; puirified by fractional recrystn. from petroleum ether and CH2Cl2 (2:1), identified by absorption and OPC spectra;

trans-(RR,SS)-bis(isothiocyanato)(1,5,8,12-tetraazadodecane)chromium(III) thiocyanate (81688-81-5) + (-)-O,O′-dibenzoyl-L-tartaric acid monohydrate (62708-56-9) → (-)589-trans-(RR)-[Cr(NCS)2(3,2,3-tet)][HBzOT] (81738-86-5)

Conditions	Yield
With lithium hydroxide; formic acid In water chiral acid was treated with LiOH in water at 60°C; filtration, pH adjusting to <8 with formic acid: prepd. soln. was added to soln. of Cr complex in buffer at 60°C; cooling to room temp. for 1-2 h;

oxalato(1,5,8,12-tetraazadodecane)chromium(III) perchlorate monohydrate + (-)-O,O′-dibenzoyl-L-tartaric acid monohydrate (62708-56-9) → Δ(-)589-cis-β-(RR)-[Cr(ox)(3,2,3-tet)][HBzOT]*H2O (81739-55-1)

Conditions	Yield
With lithium hydroxide; formic acid In water chiral acid was treated with LiOH in water at 60°C; filtration, pH adjusting to <8 with formic acid: prepd. soln. was added to soln. of Cr complex in buffer at 60°C; cooling to room temp. for 1-2 h; collection, washing with i-PrOH and ether, air-drying; elem. anal.;

(R)-α-bromo-2-chlorophenylacetic acid (256398-61-5) + copper(II) acetate monohydrate (6046-93-1) + (-)-O,O′-dibenzoyl-L-tartaric acid monohydrate (62708-56-9) → Cu2(L-O,O'-dibenzoyltartrate)((R)-α-bromo-2-chlorophenylacetate)(OAc)(H2O)2

Conditions	Yield
In ethanol; water EtOH-H2O (3:1), 40°C, 1 day; cooling to -10°C; elem. anal.;

(R)-α-bromo-2-chlorophenylacetic acid (256398-61-5) + copper(II) acetate monohydrate (6046-93-1) + (-)-O,O′-dibenzoyl-L-tartaric acid monohydrate (62708-56-9) + acetonitrile (75-05-8) → [Cu2(L-O,O'-dibenzoyltartrate)((S)-α-bromo-2-chlorophenylacetate)(OAc)(H2O)2]*1.5MeCN + [Cu2(L-O,O'-dibenzoyltartrate)((R)-α-bromo-2-chlorophenylacetate)(OAc)(H2O)2]*1.5MeCN

Conditions	Yield
In acetonitrile to soln. L-O,O'-dibenzoyltartaric acid*H2O and α-halocarboxylic acid in MeCN at 40°C was added Cu(OAc)2*H2O, mixt. was stirred for 2 days;	A n/a B 0%

2‑(1,6,7,8‑tetrahydro‑2H‑indeno[5,4‑b]furan‑8‑yl)ethylamine hydrochloride (1053239-39-6) + (-)-O,O′-dibenzoyl-L-tartaric acid monohydrate (62708-56-9) → (S)-2-(1,6,7,8-tetrahydro-2H-indeno[5,4-b]furan-8-yl)ethylamine dibenzoyl-L-tartaric acid

Conditions	Yield
Stage #1: 2‑(1,6,7,8‑tetrahydro‑2H‑indeno[5,4‑b]furan‑8‑yl)ethylamine hydrochloride With sodium hydroxide In dichloromethane; water Stage #2: (-)-O,O′-dibenzoyl-L-tartaric acid monohydrate In acetonitrile at 60℃;

Downstream Products

• 1478192-74-3 (-)-R,R-2,8-dibromo-6,12-dihydro-5,11-methanodibenzo-[b,f ][1,5]diazocine*(-)-O,O′-dibenzoyl-L-tartaric acid 
• 1478192-97-0 (-)-R,R-2-bromo-6,12-dihydro-5,11-methanodibenzo[b,f ]-[1,5]diazocine*(-)-O,O′-dibenzoyl-L-tartaric acid 
• 1478192-90-3 (-)-R,R-2-iodo-6,12-dihydro-5,11-methanodibenzo[b,f ][1,5]-diazocine*(-)-O,O′-dibenzoyl-L-tartaric acid 
• 1478259-27-6 (-)-R,R-2,8-dichloro-6,12-dihydro-5,11-methanodibenzo-[b,f ][1,5]diazocine*(-)-O,O′-dibenzoyl-L-tartaric acid 
• 1478192-79-8 (-)-R,R-2,8-diiodo-6,12-dihydro-5,11-methanodibenzo[b,f ]-[1,5]diazocine*(-)-O,O′-dibenzoyl-L-tartaric acid 
• 1202533-76-3 (-)-R,R-2,8-dimethoxy-6,12-dihydro-5,11-methanodibenzo-[b,f ][1,5]diazocine*(-)-O,O′-dibenzoyl-L-tartaric acid 
• 900804-66-2 (-)-R,R-2,8-dimethyl-6,12-dihydro-5,11-methanodibenzo-[b,f ][1,5]diazocine*(-)-O,O′-dibenzoyl-L-tartaric acid 
• 81739-55-1 Δ(-)589-cis-β-(RR)-[Cr(ox)(3,2,3-tet)][HBzOT]*H2O 
• 81738-86-5 (-)589-trans-(RR)-[Cr(NCS)2(3,2,3-tet)][HBzOT]