Acetic Acid Mixture with Hydrobromic Acid → HCID 13178442, compound

HRID 1981415Notes

Reaction equation

HRID 1981415 reaction equation
Br.C(O)(=O)C.CS(O)(=O)=O.C(OC([NH:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][C:30]1[CH:35]=[CH:34][C:33]([C:36](=[NH:38])[NH2:37])=[CH:32][C:31]=1[C:39](=[O:46])[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)=[O:28])=O)C1C=CC=CC=1>C(OCC)C>[NH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][C:27]([O:29][C:30]1[CH:35]=[CH:34][C:33]([C:36](=[NH:37])[NH2:38])=[CH:32][C:31]=1[C:39](=[O:46])[C:40]1[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=1)=[O:28]

Participants

4

Reactant 2

HCID 21893785Acetic Acid Mixture with Hydrobromic AcidHCID 86740068HCID 86740068, compound

Product 1

HCID 13178442HCID 13178442, compoundYield 87.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To 8.0 ml of a 30% hydrogen bromide-acetic acid mixture, was added 1.7 g of 4-amidino-2-benzoylphenyl 6-benzyloxycarbonylaminocaproate methanesulfonate. The mixture was stirred for one hour at room temperature, whereby the crystals dissolved in 4 to 5 minutes, forming a uniform solution. Upon addition of anhydrous ethyl ether to the solution, an oily substance separated out. The supernatant was removed and the oily substance was washed a few times with ethyl ether. The oily substance was dissolved with heating in a small volume of water, admixed with acetone, and stirred while cooling in ice, to obtain 0.9 g of a colorless powder of 4-amidino-2-benzoylphenyl 6-aminocaproate dihydrobromide.

Workup

  1. dissolutionwhereby the crystals dissolved in 4 to 5 minutes
  2. customforming a uniform solution
  3. customan oily substance separated out
  4. customThe supernatant was removed
  5. washthe oily substance was washed a few times with ethyl ether
  6. dissolutionThe oily substance was dissolved
  7. temperaturewith heating in a small volume of water
  8. stirringstirred
  9. temperaturewhile cooling in ice

Sources & evidence

ORD record
ord-9a1a3991ecd6470e8fc209aef39486a9
Source dataset
uspto-grants-1985_04
Patent number
US04514416

Reaction notes

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