Pyridine → HCID 178479470, compound

HRID 2119024Notes

Reaction equation

HRID 2119024 reaction equation
[ClH:1].[NH:2]([CH2:6][C@H:7]1[CH2:12][CH2:11][C@H:10]([C:13]([OH:15])=O)[CH2:9][CH2:8]1)[C:3]([NH2:5])=[NH:4].[C:16]([O:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1)(=[O:24])[C:17]1[C:18](=[CH:20][CH:21]=[CH:22][CH:23]=1)[NH2:19].N1C=CC=CC=1.C1(N=C=NC2CCCCC2)CCCCC1>O>[ClH:1].[CH2:26]([O:25][C:16]([C:17]1[CH:23]=[CH:22][CH:21]=[CH:20][C:18]=1[NH:19][C:13]([C@H:10]1[CH2:9][CH2:8][C@H:7]([CH2:6][NH:2][C:3]([NH2:5])=[NH:4])[CH2:12][CH2:11]1)=[O:15])=[O:24])[C:27]1[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 10868DicyclohexylcarbodiimideHCID 522771Benzyl anthranilateHCID 178479474HCID 178479474, compound

Product 1

HCID 178479470HCID 178479470, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Trans-4-guanidinomethylcyclohexanecarboxylic acid hydrochloride (3.0 g, 0.013 mole) (which is prepared by the method as disclosed in Japanese Patent First Publication No. 19694/1977, C.A., 87, 53269x) and benzyl anthranilate (3.4 g, 0.015 mole) are added to pyridine (25 ml), and thereto is added dicyclohexylcarbodiimide (3.1 g, 0.015 mole), and the mixture is stirred at room temperature for 72 hours. After the completion of the reaction, water (10 ml) is added to the reaction mixture, and the mixture is stirred for 30 minutes, and the undissolved materials are filtered off. The filtrate is concentrated to driness. The resulting residue is washed with ethyl acetate (100 ml) and recrystallized from water to give N-(o-benzyloxycarbonylphenyl)-trans-4-guanidinomethylcyclohexanecarboxamide hydrochloride (3.2 g) as white crystals. m.p. 93°-95° C.

Workup

  1. additionis added to the reaction mixture
  2. stirringthe mixture is stirred for 30 minutes
  3. filtrationthe undissolved materials are filtered off
  4. concentrationThe filtrate is concentrated to driness
  5. washThe resulting residue is washed with ethyl acetate (100 ml)
  6. customrecrystallized from water

Sources & evidence

ORD record
ord-7b8dfbee549848a09ab367860088d6cc
Source dataset
uspto-grants-1987_07
Patent number
US04681895

Reaction notes

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