Methanol → HCID 3068124, compound

HRID 1262995Notes

Reaction equation

HRID 1262995 reaction equation
CO.CS(O)(=O)=O.C(OC([NH:18][CH2:19][C:20]1[CH:41]=[CH:40][C:23]([C:24]([O:26][C:27]2[CH:36]=[CH:35][C:34]3[C:29](=[CH:30][CH:31]=[C:32]([C:37](=[NH:39])[NH2:38])[CH:33]=3)[CH:28]=2)=[O:25])=[CH:22][CH:21]=1)=O)C1C=CC=CC=1.CS(O)(=O)=O.[H][H]>[Pd].CN(C=O)C>[NH2:18][CH2:19][C:20]1[CH:21]=[CH:22][C:23]([C:24]([O:26][C:27]2[CH:36]=[CH:35][C:34]3[C:29](=[CH:30][CH:31]=[C:32]([C:37](=[NH:38])[NH2:39])[CH:33]=3)[CH:28]=2)=[O:25])=[CH:40][CH:41]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 6395Methanesulfonic AcidHCID 13176888HCID 13176888, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 3068124HCID 3068124, compoundYield 103.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solvent mixture comprising100 ml of methanol and 20 ml of DMF, were added 5.0 g 6-amidino-2-naphthyl 4-benzyloxycarbonylaminomethylbenzoate methanesulfonate, 1.0 g of 10% Pd-C and 1.1 g of methanesulfonic acid. Hydrogen was introduced into the mixture with vigorous stirring for 3 hours. After completion of the reaction, the reaction mixture was filtered and the filtrate was concentrated to about half the volume. Ethyl ether was added to the concentrate and the precipitated crystals were collected by filtration to obtain 3.0 g of a white powder of 6-amidino-2-naphthyl 4-aminomethylbenzoate dimethanesulfonate.

Workup

  1. customAfter completion of the reaction
  2. filtrationthe reaction mixture was filtered
  3. concentrationthe filtrate was concentrated to about half the volume
  4. additionEthyl ether was added to the
  5. concentrationconcentrate
  6. filtrationthe precipitated crystals were collected by filtration

Sources & evidence

ORD record
ord-5ae5258e1360402a94d2975675f1579e
Source dataset
uspto-grants-1984_06
Patent number
US04454338

Reaction notes

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