p-Toluenesulfonic acid monohydrate → HCID 178487532, compound

HRID 1833785Notes

Reaction equation

HRID 1833785 reaction equation
[N:1]#[N:2].[CH3:3][O:4][C:5]1[CH:14]=[C:13]2[C:8]([CH:9]=[CH:10][C:11]([S:15]([NH:18][C@H:19]([C:27]([OH:29])=[O:28])[CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:26])[NH2:25])(=[O:17])=[O:16])=[CH:12]2)=[CH:7][CH:6]=1.O.[C:31]1([CH3:41])[CH:36]=[CH:35][C:34]([S:37]([OH:40])(=[O:39])=[O:38])=[CH:33][CH:32]=1>C(O)C1C=CC=CC=1.C1C=CC=CC=1>[N:1]#[N:2].[C:31]1([CH3:41])[CH:32]=[CH:33][C:34]([S:37]([OH:40])(=[O:38])=[O:39])=[CH:35][CH:36]=1.[CH2:41]([O:28][C:27](=[O:29])[C@H:19]([CH2:20][CH2:21][CH2:22][NH:23][C:24](=[NH:25])[NH2:26])[NH:18][S:15]([C:11]1[CH:10]=[CH:9][C:8]2[C:13](=[CH:14][C:5]([O:4][CH3:3])=[CH:6][CH:7]=2)[CH:12]=1)(=[O:16])=[O:17])[C:31]1[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 178487531HCID 178487531, compound

Product 1

HCID 178487532HCID 178487532, compoundYield 94%

Reagents, catalysts & solvents 2

HCID 241BenzeneSolventHCID 244Benzyl AlcoholSolvent

Procedure

A mixture of 1.0 gram of N2 -(7-methoxy-2-naphthalenesulfonyl) -L-arginine, 1.0 gram of p-toluenesulfonic acid monohydrate in 5 ml of benzyl 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 cystalline mass of N2 -(7-methoxy-2-naphthalenesulfonyl)-L-arginine benzyl ester p-toluenesulfonate in 94% yield; mp. 115° - 117°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-ee3dcba4ea3e4083a2a4f2203c3d37e1
Source dataset
uspto-grants-1978_01
Patent number
US04066758

Reaction notes

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