Methanesulfonic Acid → HCID 13146258, compound

HRID 2413222Notes

Reaction equation

HRID 2413222 reaction equation
CS(O)(=O)=O.C(OC([NH:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[C:30]([C:35](=[NH:37])[NH2:36])[CH:31]=2)[CH:26]=1)=[O:23])=O)C1C=CC=CC=1.CS(O)(=O)=O.[H][H]>[C].[Pd].CN(C)C=O>[NH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][C:22]([O:24][C:25]1[CH:34]=[CH:33][C:32]2[C:27](=[CH:28][CH:29]=[C:30]([C:35](=[NH:36])[NH2:37])[CH:31]=2)[CH:26]=1)=[O:23]

Participants

6

Reactant 3

HCID 6395Methanesulfonic AcidHCID 13146257HCID 13146257, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13146258HCID 13146258, compoundYield 36.6%

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 6228DimethylformamideSolvent

Procedure

To 40 ml of anhydrous dimethylformamide, were added 4.2 g of 6-amidino-2-naphthyl ε-benzyloxycarbonylaminocaproate methanesulfonate, 1.0 g of methanesulfonic acid, and 0.2 g of 10% palladium-carbon. Hydrogen was passed for 4 hours through the vigorously stirred mixture. After removing the palladium-carbon by filtration, the filtrate was poured into stirred ethyl ether. An oily substance which separated out was washed with ethyl ether and recrystallized from ethanol to obtain 0.87 g of white crystals of 6-amidino-2-naphthyl ε-aminocaproate dimethanesulfonate.

Workup

  1. customAfter removing the palladium-carbon
  2. filtrationby filtration
  3. additionthe filtrate was poured
  4. customAn oily substance which separated out
  5. washwas washed with ethyl ether
  6. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-6ff04bc586f9405192faf7f5ae35f1de
Source dataset
uspto-grants-1985_01
Patent number
US04496584

Reaction notes

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