Dicyclohexylcarbodiimide → HCID 22865581, compound

HRID 743881Notes

Reaction equation

HRID 743881 reaction equation
Cl.[CH2:2]([O:9][C:10](=[O:16])[C@@H:11]1[CH2:15][CH2:14][CH2:13][NH:12]1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH:17](N(C(C)C)CC)(C)C.ON1[C:31]2[CH:32]=[CH:33][CH:34]=[CH:35][C:30]=2N=N1.[N:36]1[NH:37][N:38]=[N:39][C:40]=1[C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][C:42]=1[C:47]1[CH:65]=[CH:64][C:50]2[N:51]([CH:54]([CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])[C:55](O)=[O:56])[CH:52]=[N:53][C:49]=2[CH:48]=1.C1(N=C=NC2CCCCC2)CCCCC1>CN(C=O)C.C(OCC)(=O)C.O>[CH2:2]([O:9][C:10](=[O:16])[C@:11]1([CH2:17][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[CH2:15][CH2:14][CH2:13][N:12]1[C:55](=[O:56])[CH:54]([N:51]1[C:50]2[CH:64]=[CH:65][C:47]([C:42]3[CH:43]=[CH:44][CH:45]=[CH:46][C:41]=3[C:40]3[N:36]=[N:37][NH:38][N:39]=3)=[CH:48][C:49]=2[N:53]=[CH:52]1)[CH2:58][CH2:59][CH2:60][CH2:61][CH2:62][CH3:63])[C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

9

Reactant 5

HCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 81531DiisopropylethylamineHCID 2733413Proline benzyl ester hydrochlorideHCID 158381802-[5-[2-(2H-tetrazol-5-yl)phenyl]benzimidazol-1-yl]octanoic acid

Product 1

HCID 22865581HCID 22865581, compoundYield 0%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

L-proline benzyl ester hydrochloride (0.745 moles, 180 mg) and diisopropylethyl amine (0.745 moles, 0.13 ml) were dissolved in 50 ml DMF. The solution was stirred at room temperature for 20 minutes. 1-Hydroxybenzotriazole (0.745 moles, 100 mg), 2-[5-[2-(2H-tetrazol-5yl)phenyl]benzimidazol-1-yl]octanoic acid (0.745 moles, 300 mg) and dicyclohexylcarbodiimide (0.745 mmoles, 153 mg) were added sequentially. The reaction was stirred at room temperature for 12 days and poured into water. Ethyl acetate was added, washed with brine, dried over sodium sulfate, concentrated and purified by chromatography over silica gel eluted with ethyl acetate. The reaction yielded 250 mg of benzyl 1-[1-oxo-2-[5-[2-(2H-tetrazol-5yl)phenyl]-1H-benzimidazole-1-yl]octyl]-L-proline benzyl ester. (MS)

Workup

  1. stirringThe reaction was stirred at room temperature for 12 days
  2. washwashed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated
  5. custompurified by chromatography over silica gel
  6. washeluted with ethyl acetate

Sources & evidence

ORD record
ord-b7170a02ed874178b61983dc3dafc4a1
Source dataset
uspto-grants-1996_09
Patent number
US05556981

Reaction notes

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