p-Toluenesulfonic acid monohydrate → HCID 178451192, compound

HRID 2163369Notes

Reaction equation

HRID 2163369 reaction equation
[N:1]#[N:2].[CH3:3][O:4][C:5]1[CH:6]=[C:7]2[C:12](=[CH:13][C:14]=1[O:15][CH3:16])[CH:11]=[C:10]([S:17]([NH:20][C@H:21]([C:29]([OH:31])=[O:30])[CH2:22][CH2:23][CH2:24][NH:25][C:26](=[NH:28])[NH2:27])(=[O:19])=[O:18])[CH:9]=[CH:8]2.O.[C:33]1([CH3:43])[CH:38]=[CH:37][C:36]([S:39]([OH:42])(=[O:41])=[O:40])=[CH:35][CH:34]=1>C(O)CCC.C1C=CC=CC=1>[N:1]#[N:2].[C:33]1([CH3:43])[CH:34]=[CH:35][C:36]([S:39]([OH:42])(=[O:40])=[O:41])=[CH:37][CH:38]=1.[CH2:38]([O:30][C:29](=[O:31])[C@H:21]([CH2:22][CH2:23][CH2:24][NH:25][C:26](=[NH:27])[NH2:28])[NH:20][S:17]([C:10]1[CH:9]=[CH:8][C:7]2[C:12](=[CH:13][C:14]([O:15][CH3:16])=[C:5]([O:4][CH3:3])[CH:6]=2)[CH:11]=1)(=[O:18])=[O:19])[CH2:33][CH2:34][CH3:35]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 178486646HCID 178486646, compound

Product 1

HCID 178451192HCID 178451192, compoundYield 92%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 2631-ButanolSolvent

Procedure

A mixture of 1.0 g of N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginine and 1.0 g of p-toluenesulfonic acid monohydrate in 5 ml of butyl alcohol and 30 ml of benzene was refluxed for 5 hours, while removing the water formed during the reaction. The reaction mixture was concentrated under reduced pressure, and to the residue was added ethyl ether to yield a crystalline substance which was collected by filtration, washed several times with ethyl ether to afford N2 -(6,7-dimethoxy-2-naphthalenesulfonyl)-L-arginine butyl ester p-toluenesulfonate: yield 92%, m.p. 113-115° C.

Workup

  1. temperaturewas refluxed for 5 hours
  2. customwhile removing the water
  3. customformed during the reaction
  4. concentrationThe reaction mixture was concentrated under reduced pressure
  5. additionto the residue was added ethyl ether
  6. customto yield a crystalline substance which
  7. filtrationwas collected by filtration
  8. washwashed several times with ethyl ether

Sources & evidence

ORD record
ord-6c90bd1495ab480288d75c9ca28802ae
Source dataset
uspto-grants-1979_01
Patent number
US04133880

Reaction notes

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