2-Benzoylbenzoic Acid → HCID 53808064, compound

HRID 1457330Notes

Reaction equation

HRID 1457330 reaction equation
[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([OH:13])=O)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.ON1C2C=CC=CC=2N=N1.Cl.[CH3:30][O:31][C:32](=[O:38])[C@@H:33]1[CH2:37][CH2:36][CH2:35][NH:34]1.CCN(C(C)C)C(C)C.C1(N=C=NC2CCCCC2)CCCCC1>C(Cl)Cl>[CH3:30][O:31][C:32](=[O:38])[C@@H:33]1[CH2:37][CH2:36][CH2:35][N:34]1[C:11](=[O:13])[C:10]1[CH:14]=[CH:15][CH:16]=[CH:17][C:9]=1[C:1](=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 5

HCID 68132-Benzoylbenzoic AcidHCID 10868DicyclohexylcarbodiimideHCID 81531DiisopropylethylamineHCID 2733200methyl L-prolinate hydrochlorideHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 53808064HCID 53808064, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
10 °C

Procedure

6.20 g (27.5 mmol) of o-benzoylbenzoic acid was dissolved in 150 ml of methylene chloride at 25° C. under a nitrogen atmosphere. The solution was cooled to 10° C. and 4.08 g (30.2 mmol) of 1-hydroxybenzotriazole hydrate was added, followed by 5.0 g (30.2 mmol) of L-proline methyl ester HCl and followed by 6.22 g (30.2 mmol) of N,N'-diisopropylethylamine. Lastly, 6.22 g (30.2 mmol) N,N'-dicyclohexylcarbodiimide (DCC) was added which produced a slight exothermic reaction and the mixture was then stirred for 12 hours, after which time tlc analysis indicated complete consumption of starting material. A standard work-up was performed which involved removing precipitated urea by filtration and washing the filtrate with 5% sodium bicarbonate solution, 1N sodium hydroxide solution, 1N hydrochloric acid and brine. The organic phase was dried over magnesium sulfate and evaporated in vacuo to afford a yellow residue. Purification by flash chromatography on silica gel (40:1/methylene chloride:methanol) gave a yield of 6.4 g (69%) of the title compound as a cloudy gum which crystallized on standing. TLC (90:10/CH2Cl2 :MeOH): Rf =0.80. mp=128-130. 1H NMR (CDCl3) δ: 7.40-7.85(m,9H); 4.25-4.55(m,1H); 3.40-3.75(m,5H); 1.85-2.40(m,4H). I.R. (KBr): 1622, 1661, 1739, 1745 cm-1. Standard Combustion Analysis: C,71.20; H,5.68; N,4.15. Found: C,70.63; H,5.53; N=4.36. High Resolution Mass Spectrum: m/e=338.1384±0.8 ppm (calculated for C20H20NO).

Workup

  1. customproduced
  2. customa slight exothermic reaction
  3. customconsumption of starting material
  4. custominvolved removing
  5. customprecipitated urea
  6. filtrationby filtration
  7. washwashing the filtrate with 5% sodium bicarbonate solution, 1N sodium hydroxide solution, 1N hydrochloric acid and brine
  8. dry with materialThe organic phase was dried over magnesium sulfate
  9. customevaporated in vacuo
  10. customto afford a yellow residue
  11. customPurification by flash chromatography on silica gel (40:1/methylene chloride:methanol)

Sources & evidence

ORD record
ord-d55d30d6edb14155a454926fc1511816
Source dataset
uspto-grants-1998_12
Patent number
US05847155

Reaction notes

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