Dimethylformamide → 6-Amidino-2-naphthyl 5-(4-carboxybutyrylaminomethyl)furan-2-carboxylate methanesulfonate

HRID 1734112Notes

Reaction equation

HRID 1734112 reaction equation
CN(C=O)C.Cl.[C:7]([CH2:10][CH2:11][CH2:12][C:13]([NH:15][CH2:16][C:17]1[O:21][C:20]([C:22]([O:24][C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[C:30]([C:35](=[NH:37])[NH2:36])[CH:31]=3)[CH:26]=2)=[O:23])=[CH:19][CH:18]=1)=[O:14])([OH:9])=[O:8].[CH3:38][S:39]([OH:42])(=[O:41])=[O:40]>CC(C)=O>[CH3:38][S:39]([OH:42])(=[O:41])=[O:40].[C:7]([CH2:10][CH2:11][CH2:12][C:13]([NH:15][CH2:16][C:17]1[O:21][C:20]([C:22]([O:24][C:25]2[CH:34]=[CH:33][C:32]3[C:27](=[CH:28][CH:29]=[C:30]([C:35](=[NH:36])[NH2:37])[CH:31]=3)[CH:26]=2)=[O:23])=[CH:19][CH:18]=1)=[O:14])([OH:9])=[O:8]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 6395Methanesulfonic AcidHCID 98254776-Amidino-2-naphthyl 5-(4-carboxybutyrylaminomethyl)furan-2-carboxylate hydrochloride

Product 1

HCID 223988436-Amidino-2-naphthyl 5-(4-carboxybutyrylaminomethyl)furan-2-carboxylate methanesulfonateYield 68.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To 10 ml of DMF was added 2.0 g of 6-amidino-2-naphthyl 5-(4-carboxybutyrylaminomethyl)furan-2-carboxylate hydrochloride, then 4.6 g of methanesulfonic acid was added dropwise while cooling with ice, and the mixture was stirred for 10 minutes. Then, the mixture was added in small portions into 400 ml of acetone and stirred for 4 hours while cooling with ice. The supernatant was decanted, 1 l of ether was added to the residue and stirred, and the precipitate was collected by filtration to obtain 1.54 g of the intended product.

Workup

  1. temperaturewhile cooling with ice
  2. stirringstirred for 4 hours
  3. temperaturewhile cooling with ice
  4. customThe supernatant was decanted
  5. addition1 l of ether was added to the residue
  6. stirringstirred
  7. filtrationthe precipitate was collected by filtration

Sources & evidence

ORD record
ord-c8087508363c49c39cbd8964f431febf
Source dataset
uspto-grants-1996_07
Patent number
US05532267

Reaction notes

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