p-Toluenesulfonic acid monohydrate → HCID 178451194, compound

HRID 2072185Notes

Reaction equation

HRID 2072185 reaction equation
[N:1]#[N:2].[N+:3]([C:6]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:7]=1[CH:8]=[CH:9][CH:10]=[C:11]2[S:16]([NH:19][C@H:20]([C:28]([OH:30])=[O:29])[CH2:21][CH2:22][CH2:23][NH:24][C:25](=[NH:27])[NH2:26])(=[O:18])=[O:17])([O-:5])=[O:4].O.[C:32]1([CH3:42])[CH:37]=[CH:36][C:35]([S:38]([OH:41])(=[O:40])=[O:39])=[CH:34][CH:33]=1>C(O)CCC.C1C=CC=CC=1>[N:1]#[N:2].[C:32]1([CH3:42])[CH:33]=[CH:34][C:35]([S:38]([OH:41])(=[O:39])=[O:40])=[CH:36][CH:37]=1.[CH2:37]([O:29][C:28](=[O:30])[C@H:20]([CH2:21][CH2:22][CH2:23][NH:24][C:25](=[NH:26])[NH2:27])[NH:19][S:16]([C:11]1[C:12]2[C:7](=[C:6]([N+:3]([O-:5])=[O:4])[CH:15]=[CH:14][CH:13]=2)[CH:8]=[CH:9][CH:10]=1)(=[O:18])=[O:17])[CH2:32][CH2:33][CH3:34]

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 178514633HCID 178514633, compound

Product 1

HCID 178451194HCID 178451194, compoundYield 95%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 2631-ButanolSolvent

Procedure

A mixture of 1.0 gram of N2 -(5-nitro-1-naphthalenesulfonyl)-L-arginine, 1.0 gram of p-toluenesulfonic acid monohydrate in 5 ml of n-butyl alcohol and 30 ml of benzene was refluxed for 5 hours, removing water by azeotropic distillation. After the solvent was removed by distillation, 100 ml of ethyl ether was added to the residue, giving a crystalline mass of N2 -(5-nitro-1-naphthalenesulfonyl)-L-arginine butyl ester p-toluenesulfonate in 95% yield; mp. 94° - 95° C.

Workup

  1. temperaturewas refluxed for 5 hours
  2. customremoving water
  3. distillationby azeotropic distillation
  4. customAfter the solvent was removed by distillation, 100 ml of ethyl ether
  5. additionwas added to the residue

Sources & evidence

ORD record
ord-82e201e9ea13499d8ab99287bd9dae85
Source dataset
uspto-grants-1977_09
Patent number
US04049645

Reaction notes

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