Dicyclohexylcarbodiimide → 4-Amidino-2-benzoylphenyl 4-benzyloxybenzoate

HRID 1589501Notes

Reaction equation

HRID 1589501 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:12]([C:13]([OH:15])=[O:14])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1CCC(N=C=NC2CCCCC2)CC1.CS(O[C:38]1[CH:43]=[CH:42][C:41]([C:44](=[NH:46])[NH2:45])=[CH:40][C:39]=1[C:47](=[O:54])[C:48]1[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=1)(=O)=O>N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:13]([O:15][C:38]2[CH:43]=[CH:42][C:41]([C:44](=[NH:45])[NH2:46])=[CH:40][C:39]=2[C:47](=[O:54])[C:48]2[CH:53]=[CH:52][CH:51]=[CH:50][CH:49]=2)=[O:14])=[CH:16][CH:17]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 10868DicyclohexylcarbodiimideHCID 738804-(Benzyloxy)benzoic acidHCID 540991824-Amidino-2-benzoylphenol methanesulfonate

Product 1

HCID 131784714-Amidino-2-benzoylphenyl 4-benzyloxybenzoateYield 77.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture of 3.4 g of 4-benzyloxybenzoic acid and 50 ml of dried pyridine, while being cooled in ice, was added 3.7 g of DCC. After having been stirred for 30 minutes, the mixture was admixed with 5.0 g of 4-amidino-2-benzoylphenol methanesulfonate and stirred overnight at room temperature. The reaction mixture was freed from the insolubles by filtration and mixed with ethyl ether. The precipitated insoluble substance was recrystallized from a methanol-ethyl ether mixture to obtain 5.2 g of colorless crystals of 4-amidino-2-benzoylphenyl 4-benzoyloxybenzoate methanesulfonate.

Workup

  1. temperaturewhile being cooled in ice
  2. stirringstirred overnight at room temperature
  3. filtrationThe reaction mixture was freed from the insolubles by filtration
  4. additionmixed with ethyl ether
  5. customThe precipitated insoluble substance was recrystallized from a methanol-ethyl ether mixture

Sources & evidence

ORD record
ord-c5ebe925520f4148b5aaccff6ff96513
Source dataset
uspto-grants-1986_02
Patent number
US04570006

Reaction notes

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