Acetate → HCID 178476464, compound

HRID 2119029Notes

Reaction equation

HRID 2119029 reaction equation
Cl.[CH2:2]([O:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]([C@H:16]1[CH2:21][CH2:20][C@H:19]([CH2:22][NH:23][C:24]([NH2:26])=[NH:25])[CH2:18][CH2:17]1)=[O:15])=[O:6])[CH3:3].C([O-])(=O)C>O.CO>[C:5]([OH:6])(=[O:4])[CH3:7].[CH2:2]([O:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[NH:13][C:14]([C@H:16]1[CH2:21][CH2:20][C@H:19]([CH2:22][NH:23][C:24]([NH2:26])=[NH:25])[CH2:18][CH2:17]1)=[O:15])=[O:6])[CH3:3]

Participants

4

Reactant 2

HCID 175AcetateHCID 178468799HCID 178468799, compound

Product 1

HCID 178476464HCID 178476464, compoundYield 147.6%

Reagents, catalysts & solvents 1

HCID 22242641Methanol--water (1/1)Solvent

Procedure

N-(o-Ethoxycarbonylphenyl)-trans-4-guanidinomethylcyclohexanecarboxamide hydrochloride (370 mg, 0.001 mole) prepared in Example 1 is dissolved in a mixture of water-methanol (1:1) and thereto is added ion exchange resin (Amberlite®IRA-400, manufactured by Rohm & Haas, which is previously converted into acetate type) (15 ml), and the mixture is stirred at room temperature overnight. After filtering off the resin, the filtrate is concentrated and recrystallized from water to give the title compound (300 mg) as white crystals. m.p. 212°-214° C.

Workup

  1. additionis added ion exchange resin (Amberlite®IRA-400
  2. filtrationAfter filtering off the resin
  3. concentrationthe filtrate is concentrated
  4. customrecrystallized from water

Sources & evidence

ORD record
ord-bbdcbafca451439392644705dab80b92
Source dataset
uspto-grants-1987_07
Patent number
US04681895

Reaction notes

Loading…