Dicyclohexylcarbodiimide → HCID 22865581, compound

HRID 866249Notes

Reaction equation

HRID 866249 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 49.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

L-proline benzyl ester hydrochloride (0.745 mmoles, 180 mg) and diisopropylethyl amine (0.745 mmoles, 0.13 ml) were dissolved in 50 ml DMF. The solution was stirred at room temperature for 20 minutes. 1-Hydroxybenzotriazole (0.745 mmoles, 100 mg), 2-[5-[2-(2H-tetrazol-5-yl)phenyl]benzimidazol-1-yl]octanoic acid (0.745 mmoles, 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-5-yl)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-641e36423d9f4a728141b3bd384522e7
Source dataset
uspto-grants-1996_10
Patent number
US05569768

Reaction notes

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