2-Benzoylbenzoic Acid → HCID 53664777, compound

HRID 1457333Notes

Reaction equation

HRID 1457333 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.C1CCC(N=C=NC2CCCCC2)CC1.C[O:45][C:46](=O)[C@@H:47]1[CH2:51][CH2:50][CH2:49][NH:48]1>C(Cl)Cl>[C:1]([C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([N:48]1[CH2:49][CH2:50][CH2:51][C@H:47]1[CH2:46][OH:45])=[O:13])(=[O:8])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 68132-Benzoylbenzoic Acid2×HCID 10868DicyclohexylcarbodiimideHCID 853477Methyl L-prolinateHCID 27960291-Hydroxybenzotriazole hydrate

Product 1

HCID 53664777HCID 53664777, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.78 g (30 mmol) o-benzoylbenzoic acid and 2.96 ml (30 mmol) of S(+)-2-pyrrolidinemethanol were reacted with 4.05 g (30 mmol) 1-hydroxybenzotriazole hydrate and 6.18 g (30 mmol) of DCC in 150 ml methylene chloride as described in Example 25 for the coupling of o-benzoylbenzoic acid with L-proline methyl ester. The crude reaction mixture was washed with 5% sodium bicarbonate solution, dried over anhydrous magnesium sulfate, and the solvent removed in vacuo to afford a yellow residue. Flash chromatograohy on silica gel (20:1/methylene chloride:methanol) afforded the title compound which crystallized from ethyl acetate as a white solid (3.99 g (43%)) by the addition of ether until crystallization took place. TLC (90:10/CH2Cl2 :MeOH): Rf =0.50. mp=113-114. 1H NMR (CDCl3) δ: 7.35-7.80 (9m,5H); 4.40-4.50(m,1H); 3.15-4.20(m,5H); 1.55-2.15(m,4H). I.R. (KBr): 1589, 1603, 1660 cm-1. Standard Combustion Analysis Calculated: C,73.77; H,6.19; N,4.53. Found: C,73.40; H,6.16; N,4.41. High Resolution Mass Spectrum: 309.1378±1.3 ppm (calculated for C19H19 NO3).

Workup

  1. customThe crude reaction mixture
  2. washwas washed with 5% sodium bicarbonate solution
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent removed in vacuo
  5. customto afford a yellow residue

Sources & evidence

ORD record
ord-2dc578dd78f846e4aeaf7567f14450e7
Source dataset
uspto-grants-1998_12
Patent number
US05847155

Reaction notes

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