2-Benzoylbenzoic Acid → HCID 53676546, compound

HRID 1457331Notes

Reaction equation

HRID 1457331 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.[C:18]([O:22][C:23](=[O:29])[C@@H:24]1[CH2:28][CH2:27][CH2:26][NH:25]1)([CH3:21])([CH3:20])[CH3:19].O.ON1C2C=CC=CC=2N=N1.C1CCC(N=C=NC2CCCCC2)CC1>C(Cl)Cl>[CH3:21][C:18]([O:22][C:23](=[O:29])[C@@H:24]1[CH2:28][CH2:27][CH2:26][N:25]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)([CH3:19])[CH3:20]

Participants

6

Reactant 4

HCID 68132-Benzoylbenzoic Acid2×HCID 10868DicyclohexylcarbodiimideHCID 27960291-Hydroxybenzotriazole hydrateHCID 6453108L-Proline 1,1-dimethylethyl ester2×

Product 1

HCID 53676546HCID 53676546, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

6.78 g (30mmol) of o-benzoylbenzoic acid, 5.13 g (30 mmol) of L-proline t-butyl ester, 4.05 g (30 mmol) of 1-hydroxybenzotriazole hydrate and 6.18 g (30 mmol) of DCC in 100 ml methylene chloride were reacted in the manner described in Example 25 for the coupling of o-benzoylbenzoic acid with L-proline t-butyl ester. A standard work-up as described in Example 25 afforded a viscous gum which was purified by flash chromatography on silica gel with 40:1/methylene chloride:methanol as eluant to give an amorphous solid. The isolated yield of the title compound was 8.6 g (76%). TLC (90:10/CH2Cl2 :MeOH): Rf =0.80. 1H NMR (CDCl3) δ: 7.30-7.80(m,9H,); 4.06-4.38(m,1H); 3.36-3.65(m,2H); 1.78-2.32(m,4H); 1.32(s),1.43(s,9H). I.R. (KBr): 1595, 1627, 1661, 1733 cm-1. Low Resolution Mass Spectrum: 380 (p+1). Standard Combustion Analysis Calculated: C,72.80; H,6.64; N,3.69. Found: C,72.37; H,6.59; N,3.76.

Workup

  1. customafforded a viscous gum which
  2. customwas purified by flash chromatography on silica gel with 40:1/methylene chloride
  3. custommethanol as eluant to give an amorphous solid

Sources & evidence

ORD record
ord-637fb5834f9a408a8580c11a775e922e
Source dataset
uspto-grants-1998_12
Patent number
US05847155

Reaction notes

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