HCID 86739496, compound → HCID 13176942, compound

HRID 371435Notes

Reaction equation

HRID 371435 reaction equation
[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[C:6]([O:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[C:22]([C:27](=[NH:29])[NH2:28])[CH:23]=2)[CH:18]=1)(=[O:15])[CH:7]=[CH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>CN(C=O)C.[Pd]>[CH3:1][S:2]([OH:5])(=[O:4])=[O:3].[C:9]1([CH2:8][CH2:7][C:6]([O:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[C:22]([C:27](=[NH:28])[NH2:29])[CH:23]=3)[CH:18]=2)=[O:15])[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 1

HCID 86739496HCID 86739496, compound

Product 1

HCID 13176942HCID 13176942, compoundYield 75.5%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 6228DimethylformamideSolvent

Procedure

In 30 ml of DMF, was suspended 1.2 g of 6-amidino-2-naphthyl cinnamate methanesulfonate. After addition of 0.4 g of 10% Pd-C, the mixture was subjected to catalytic hydrogenation. The reaction mixture was filtered and the filtrate was mixed with ethyl ether. The resulting precipitate was collected by filtration and recrystallized from a methanol-ethyl ether mixture to obtain 0.91 g of 6-amidino-2-naphthyl 3-phenylpropionate methanesulfonate.

Workup

  1. filtrationThe reaction mixture was filtered
  2. additionthe filtrate was mixed with ethyl ether
  3. filtrationThe resulting precipitate was collected by filtration
  4. customrecrystallized from a methanol-ethyl ether mixture

Sources & evidence

ORD record
ord-426f08f98fc542d1a6a614443dca3637
Source dataset
uspto-grants-1985_07
Patent number
US04532255

Reaction notes

Loading…