1,1'-Carbonyldiimidazole → (S)-6-(4-Benzoyl-benzoylamino)-2-carbazol-9-yl-hexanoic acid methyl ester

HRID 449757Notes

Reaction equation

HRID 449757 reaction equation
C(N1C=CN=C1)(N1C=CN=C1)=O.[C:13]([C:21]1[CH:29]=[CH:28][C:24]([C:25]([OH:27])=O)=[CH:23][CH:22]=1)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[CH3:30][O:31][C:32](=[O:52])[C@@H:33]([N:39]1[C:51]2[CH:50]=[CH:49][CH:48]=[CH:47][C:46]=2[C:45]2[C:40]1=[CH:41][CH:42]=[CH:43][CH:44]=2)[CH2:34][CH2:35][CH2:36][CH2:37][NH2:38]>C1COCC1>[CH3:30][O:31][C:32](=[O:52])[C@@H:33]([N:39]1[C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:45]=2[C:46]2[C:51]1=[CH:50][CH:49]=[CH:48][CH:47]=2)[CH2:34][CH2:35][CH2:36][CH2:37][NH:38][C:25](=[O:27])[C:24]1[CH:23]=[CH:22][C:21]([C:13](=[O:20])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 691474-Benzoylbenzoic acidHCID 67993118(S)-6-Amino-2-carbazol-9-yl-hexanoic methyl ester

Product 1

HCID 58554758(S)-6-(4-Benzoyl-benzoylamino)-2-carbazol-9-yl-hexanoic acid methyl esterYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Carbonyldiimidazole (0.162 g, 1.0 mmol) was added to a solution of 4-benzoyl benzoic acid (0.226 g, 1.0 mmol) in dry THF (10 mL) under nitrogen atmosphere at room temperature and the resulting mixture was stirred for 1 h at the same conditions. Then, (S)-methyl 6-amino-2-carbazol-9-yl-hexanoate 4 (0.310 g, 1.0 mmol) in dry THF (5 mL) was added dropwise by syringe into the reaction mixture. The reaction mixture was allowed to stir for additional 3 h at room temperature. After completion of the reaction (monitored by TLC), the solvent was removed under reduced pressure and the crude product was dissolved in ethyl acetate (50 mL) washed with brine (20 mL×2), and finally dried over anhydrous Na2SO4. Filtration followed by removal of the solvent under reduced pressure provided a gummy colorless residue, which was purified by column chromatography over silica gel using dichloromethane:methanol (98:2) as eluent to afford (S)-6-(4-benzoyl-benzoylamino)-2-carbazol-9-yl-hexanoic acid methyl ester 6 (0.290 g, 56%) as a white solid.

Workup

  1. stirringto stir for additional 3 h at room temperature
  2. customAfter completion of the reaction (monitored by TLC)
  3. customthe solvent was removed under reduced pressure
  4. dissolutionthe crude product was dissolved in ethyl acetate (50 mL)
  5. washwashed with brine (20 mL×2)
  6. dry with materialfinally dried over anhydrous Na2SO4
  7. filtrationFiltration
  8. customfollowed by removal of the solvent under reduced pressure
  9. customprovided a gummy colorless residue, which
  10. customwas purified by column chromatography over silica gel

Sources & evidence

ORD record
ord-0458709460314a4d8a41f0280a862d3d
Source dataset
uspto-grants-2013_07
Patent number
US08486534B2

Reaction notes

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